An Efficient Synthesis of 2,4-Disubstituted Quinolines by Electrophile-Mediated Cyclization Reactions of 2-Isocyanostyrene Derivatives

Bulletin of the Chemical Society of Japan

Volumn 77, Issue 3, 2004, Pages 553-559

  Kobayashi, Kazuhiro ^a   Takagoshi, Kenichi ^a   Kondo, Shizuka ^a   Morikawa, Osamu ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDES; CATALYSIS; CATALYST SELECTIVITY; DERIVATIVES; ETHERS; SALTS; SUBSTITUTION REACTIONS; SYNTHESIS (CHEMICAL);

CYCLIZATIONS REACTIONS; ELECTROPHILE-MEDIATED;

STYRENE;

2 ISOCYANOSTYRENE DERIVATIVE; ACETAL; ACETALDEHYDE; ACETONE; ALDEHYDE; ALKYL GROUP; BORON TRIFLUORIDE; ETHER; HYDROXYL GROUP; IMINE; METHYL GROUP; N,N DIMETHYLIMINIUM DERIVATIVE; NITRILE; QUINOLINE DERIVATIVE; STYRENE DERIVATIVE; STYRENE OXIDE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; CATALYST; CHEMICAL STRUCTURE; CYCLIZATION; SYNTHESIS;

EID: 1842478920     PISSN: 00092673     EISSN: None     Source Type: Journal    
DOI: 10.1246/bcsj.77.553     Document Type: Article

References (62)

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4. Recently, 2-functionalized quinoline derivatives have been prepared by reactions of 2-metalated quinolines, which were generated by direct lithiation of quinolines4a or halogen-metal exchange of 2-haloquinolines,4b,c with electrophiles: a) P. Gros, Y. Fort, and P. Caubère, J. Chem. Soc., Perkin Trans. 1, 1997, 3597.
5. b) I. Gómez, E. Alonso, D. J. Ramón, and M. Yus, Tetrahedron, 56, 4043 (2000).
6. c) S. Dumouchel, F. Mongin, F. Trécourt, and G. Quéguiner, Tetrahedron Lett., 44, 2033 (2003).
7. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
8. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
9. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
10. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
11. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
12. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
13. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
14. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
15. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
16. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
17. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
18. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
19. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
20. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
21. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
22. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
23. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
24. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
25. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
26. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
27. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
28. For recent reports on the general synthesis of quinoline derivatives: D. S. Coffey, S. A. May, and A. M. Ratz, "Progress in Heterocyclic Chemistry," ed by G. W. Gribble and T. L. Gilchrist, Pergamon, London (2001), Vol. 13, p. 243; H. Tokuyama, M. Sato, T. Ueda, and T. Fukuyama, Heterocycles, 55, 105 (2001); M. A. Fakhfakh, X. Franck, R. Hocquemiller, and B. Figadère, J. Organomet. Chem., 624, 131 (2001); H. Amii, Y. Kishikawa, and K. Uneyama, Org. Lett., 3, 1109 (2001); M. Karikomi, H. Tsukuda, and T. Toda, Heterocycles, 55, 1249 (2001); N. J. Tom and E. M. Ruel, Synthesis, 2001, 1351; M. Shimizu, A. Oishi, Y. Taguchi, T. Sano, Y. Gama, and I. Shibuya, Heterocycles, 55, 1971 (2001); C. S. Cho, J. S. Kim, T.-J. Kim, and S. C. Shim, Chem. Commun., 2001, 2576; J. N. Kim, H. J. Lee, K. Young, and H. S. Kim, Tetrahedron Lett., 42, 3737 (2001); M. A. Fakhfakh, X. Frank, A. Fournet, R. Hocquemiller, and B. Figadère, Tetrahedron Lett., 42, 3847 (2001); X. G. Li, X. Cheng, and Q. L. Zhou, Synth. Commun., 32, 2477 (2002); G. Dominguez, L. Casarrubios, J. Rodoriguez-Noriega, and J. Perez-Castells, Helv. Chim. Acta, 85, 2856 (2002); M. A. Fakhfakh, X. Franck, A. Fournet, R. Hocquemiller, and B. Figadère, Synth. Commun., 32, 2863 (2002); S. Cacchi, G. Fabrizi, A. Goggiamani, M. Moreno-Mañas, and A. Vallribera, Tetrahedron Lett., 43, 5537 (2002); J. N. Kim, Y. M. Chung, and Y. J. Im, Tetrahedron Lett., 43, 6209 (2002); H. Z. S. Huma, R. Halder, S. S. Kalra, J. Das, and J. Iqbal, Tetrahedron Lett., 43, 6485 (2002); B. S. Lee, J. H. Lee, and D. Y. Chi, J. Org. Chem., 67, 7884 (2002); R. E. Swenson, T. J. Sowin, and H. Q. Zhang, J. Org. Chem., 67, 9182 (2002); B. Jiang and Y.-G. Si, J. Org. Chem., 67, 9449 (2002); A. Arcadi, M. Chiarini, S. D. Giuseppe, and F. Marinelli, Synlett, 2003, 203; S. J. Song, S. J. Cho, D. K. Park, T. W. Kwon, and S. A. Jenekhe, Tetrahedron Lett., 44, 255 (2003); B. C. Ranu, A. Hajra, S. S. Ley, and U. Jana, Tetrahedron, 59, 813 (2003), and references cited therein.
29. For utilities of quinolines as intermediates for the design of biologically active compounds: G. Jones, "Comprehensive Heterocyclic Chemistry," ed by A. R. Katritzky and C. W. Rees, Pergamon, Oxford (1984), Vol. 2, p. 395; T. Suresh, R. N. Kumar, and P. S. Mohan, Heterocycl. Commun., 9, 83 (2003).
30. For utilities of quinolines as intermediates for the design of biologically active compounds: G. Jones, "Comprehensive Heterocyclic Chemistry," ed by A. R. Katritzky and C. W. Rees, Pergamon, Oxford (1984), Vol. 2, p. 395; T. Suresh, R. N. Kumar, and P. S. Mohan, Heterocycl. Commun., 9, 83 (2003).
31. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
32. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
33. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
34. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
35. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
36. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
37. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma,
38. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
39. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
40. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
41. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
42. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
43. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
44. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
45. For biological importance of quinoline derivatives: J. A. Joule, K. Mills, and G. F. Smith, "Heterocyclic Chemistry," 3rd ed, Chapman & Hall, London (1995), p. 120; T. Shoda, S. Taketomi, and A. Baba, Eur. Patent, 634169 (1995); Chem. Abstr., 122, 187610b (1995); M. Antini, A. Cappelli, S. Vomero, G. Giorgi, T. Langer, M. Hamon, N. Merahi, B. M. Emerit, A. Cagnotto, M. Skorupska, T. Mennini, and J. C. Pinto, J. Med. Chem., 38, 2692 (1995); P. K. Desai, P. Desai, D. Macchi, C. M. Desai, and D. Patel, Indian J. Chem., 35B, 871 (1996); X.-M. Cheng, C. Lee, S. Klutchko, T. Winters, E. E. Reynolds, K. M. Welch, M. A. Flynn, and A. M. Doherty, Bioorg. Med. Chem. Lett., 6, 2999 (1996); G. A. M. Giardina, H. M. Sarau, C. Farina, A. D. Medhurst, M. Grugni, L. F. Raveglia, D. B. Schmidt, R. Rigolio, M. Luttmann, V. Vecchietti, and D. W. P. Hay, J. Med. Chem., 40, 1794 (1997); B. Kalluraya and S. Sreevinasa, Farmaco, 53, 399 (1998); A. von Sprecher, M. Gerspacher, A. Beck, S. Kimmel, H. Weinstner, G. P. Anderson, U. Niederhauser, N. Subramanian, and M. A. Bray, Bioorg. Med. Chem. Lett., 8, 965 (1998); D. Doubé, M. Blouin, C. Brideau, C.-C. Chen, S. Desmarais, D. Eithier, J. P. Falgueyret, R. W. Frieson, M. Girard, V. Girard, J. Guay, D. Riendeau, P. Tagari, and R. N. Young, Bioorg. Med. Chem. Lett., 8, 1255 (1998); M. E. Zwaagstra, H. Timmerman, A. C. van de Stolpe, F. J. de Kanter, M. Tamura, Y. Wada, and M. Q. Zhang, J. Med. Chem., 41, 1428 (1998); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chaironi, P. Ducrot, E. Bisagni, L. Jin, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000) ; V. K. Dua, S. N. Sinha, S. Biswas, N. Valecha, S. K. Puri, and V. P. Sharma, Bioorg. Med. Chem., 12, 3587 (2002); S. Gallo, S. Atifi, A. Mahamoud, C. Santelli-Rouvier, K. Wolfárt, J. Molnar, and J. Barbe, Eur. J. Med. Chem., 38, 19 (2003); D. Varlet, E. Fourmaintraux, P. Depreux, and D. Lesieur, Heterocycles, 60, 385 (2003); L. Strekowski, M. Say, M. Henary, P. Ruiz, L. Manzel, D. E. Macfarlene, and A. J. Bojarski, J. Med. Chem., 46, 1242 (2003), and references cited therein.
46. For biological activities of 2-substituted quinoline derivatives: A. Fournet, A. A. Barrios, V. Munoz, R. Hocquemiller, A. Cavé, and J. Bruneton, Antimicrob. Agents Chemother., 37, 859 (1993); A. Fournet, M. E. Ferreira, A. Rojas de Arias, S. Torres de Ortiz, S. Fuentes, H. Nakayama, and A. Schinini, Antimicrob. Agents Chemother., 40, 2447 (1996); J. C. Gantier, A. Fournet, M. H. Munos, and R. Hocquemiller, Planta Med., 40, 285 (1996); K. Mekouar, J. F. Mouscadet, D. Desmaële, F. Subra, H. Leh, D. Savouré, C. Auclair, and J. d'Angelo, J. Med. Chem., 41, 2846 (1998); F. Zouhiri, J. F. Mouscadet, K. Mekouar, D. Desmaële, D. Savouré, H. Leh, F. Subra, M. Le Bret, C. Auclair, and J. d'Angelo, J. Med. Chem., 43, 1533 (2000); H. Nakayama, M. E. Ferreira, A. Rojas de Arias, N. V. de Bilbao, A. Schinini, and A. Fournet, Phytother. Res., 15, 630 (2001); A. Fournet, R. Mahieux, M. A. Fakhfakh, X. Frank, R. Hocquemiller, and B. Frigdère, Bioorg. Med. Chem. Lett., 13, 891 (2003).
47. For biological activities of 2-substituted quinoline derivatives: A. Fournet, A. A. Barrios, V. Munoz, R. Hocquemiller, A. Cavé, and J. Bruneton, Antimicrob. Agents Chemother., 37, 859 (1993); A. Fournet, M. E. Ferreira, A. Rojas de Arias, S. Torres de Ortiz, S. Fuentes, H. Nakayama, and A. Schinini, Antimicrob. Agents Chemother., 40, 2447 (1996); J. C. Gantier, A. Fournet, M. H. Munos, and R. Hocquemiller, Planta Med., 40, 285 (1996); K. Mekouar, J. F. Mouscadet, D. Desmaële, F. Subra, H. Leh, D. Savouré, C. Auclair, and J. d'Angelo, J. Med. Chem., 41, 2846 (1998); F. Zouhiri, J. F. Mouscadet, K. Mekouar, D. Desmaële, D. Savouré, H. Leh, F. Subra, M. Le Bret, C. Auclair, and J. d'Angelo, J. Med. Chem., 43, 1533 (2000); H. Nakayama, M. E. Ferreira, A. Rojas de Arias, N. V. de Bilbao, A. Schinini, and A. Fournet, Phytother. Res., 15, 630 (2001); A. Fournet, R. Mahieux, M. A. Fakhfakh, X. Frank, R. Hocquemiller, and B. Frigdère, Bioorg. Med. Chem. Lett., 13, 891 (2003).
48. For biological activities of 2-substituted quinoline derivatives: A. Fournet, A. A. Barrios, V. Munoz, R. Hocquemiller, A. Cavé, and J. Bruneton, Antimicrob. Agents Chemother., 37, 859 (1993); A. Fournet, M. E. Ferreira, A. Rojas de Arias, S. Torres de Ortiz, S. Fuentes, H. Nakayama, and A. Schinini, Antimicrob. Agents Chemother., 40, 2447 (1996); J. C. Gantier, A. Fournet, M. H. Munos, and R. Hocquemiller, Planta Med., 40, 285 (1996); K. Mekouar, J. F. Mouscadet, D. Desmaële, F. Subra, H. Leh, D. Savouré, C. Auclair, and J. d'Angelo, J. Med. Chem., 41, 2846 (1998); F. Zouhiri, J. F. Mouscadet, K. Mekouar, D. Desmaële, D. Savouré, H. Leh, F. Subra, M. Le Bret, C. Auclair, and J. d'Angelo, J. Med. Chem., 43, 1533 (2000); H. Nakayama, M. E. Ferreira, A. Rojas de Arias, N. V. de Bilbao, A. Schinini, and A. Fournet, Phytother. Res., 15, 630 (2001); A. Fournet, R. Mahieux, M. A. Fakhfakh, X. Frank, R. Hocquemiller, and B. Frigdère, Bioorg. Med. Chem. Lett., 13, 891 (2003).
49. For biological activities of 2-substituted quinoline derivatives: A. Fournet, A. A. Barrios, V. Munoz, R. Hocquemiller, A. Cavé, and J. Bruneton, Antimicrob. Agents Chemother., 37, 859 (1993); A. Fournet, M. E. Ferreira, A. Rojas de Arias, S. Torres de Ortiz, S. Fuentes, H. Nakayama, and A. Schinini, Antimicrob. Agents Chemother., 40, 2447 (1996); J. C. Gantier, A. Fournet, M. H. Munos, and R. Hocquemiller, Planta Med., 40, 285 (1996); K. Mekouar, J. F. Mouscadet, D. Desmaële, F. Subra, H. Leh, D. Savouré, C. Auclair, and J. d'Angelo, J. Med. Chem., 41, 2846 (1998); F. Zouhiri, J. F. Mouscadet, K. Mekouar, D. Desmaële, D. Savouré, H. Leh, F. Subra, M. Le Bret, C. Auclair, and J. d'Angelo, J. Med. Chem., 43, 1533 (2000); H. Nakayama, M. E. Ferreira, A. Rojas de Arias, N. V. de Bilbao, A. Schinini, and A. Fournet, Phytother. Res., 15, 630 (2001); A. Fournet, R. Mahieux, M. A. Fakhfakh, X. Frank, R. Hocquemiller, and B. Frigdère, Bioorg. Med. Chem. Lett., 13, 891 (2003).
50. For biological activities of 2-substituted quinoline derivatives: A. Fournet, A. A. Barrios, V. Munoz, R. Hocquemiller, A. Cavé, and J. Bruneton, Antimicrob. Agents Chemother., 37, 859 (1993); A. Fournet, M. E. Ferreira, A. Rojas de Arias, S. Torres de Ortiz, S. Fuentes, H. Nakayama, and A. Schinini, Antimicrob. Agents Chemother., 40, 2447 (1996); J. C. Gantier, A. Fournet, M. H. Munos, and R. Hocquemiller, Planta Med., 40, 285 (1996); K. Mekouar, J. F. Mouscadet, D. Desmaële, F. Subra, H. Leh, D. Savouré, C. Auclair, and J. d'Angelo, J. Med. Chem., 41, 2846 (1998); F. Zouhiri, J. F. Mouscadet, K. Mekouar, D. Desmaële, D. Savouré, H. Leh, F. Subra, M. Le Bret, C. Auclair, and J. d'Angelo, J. Med. Chem., 43, 1533 (2000); H. Nakayama, M. E. Ferreira, A. Rojas de Arias, N. V. de Bilbao, A. Schinini, and A. Fournet, Phytother. Res., 15, 630 (2001); A. Fournet, R. Mahieux, M. A. Fakhfakh, X. Frank, R. Hocquemiller, and B. Frigdère, Bioorg. Med. Chem. Lett., 13, 891 (2003).
51. For biological activities of 2-substituted quinoline derivatives: A. Fournet, A. A. Barrios, V. Munoz, R. Hocquemiller, A. Cavé, and J. Bruneton, Antimicrob. Agents Chemother., 37, 859 (1993); A. Fournet, M. E. Ferreira, A. Rojas de Arias, S. Torres de Ortiz, S. Fuentes, H. Nakayama, and A. Schinini, Antimicrob. Agents Chemother., 40, 2447 (1996); J. C. Gantier, A. Fournet, M. H. Munos, and R. Hocquemiller, Planta Med., 40, 285 (1996); K. Mekouar, J. F. Mouscadet, D. Desmaële, F. Subra, H. Leh, D. Savouré, C. Auclair, and J. d'Angelo, J. Med. Chem., 41, 2846 (1998); F. Zouhiri, J. F. Mouscadet, K. Mekouar, D. Desmaële, D. Savouré, H. Leh, F. Subra, M. Le Bret, C. Auclair, and J. d'Angelo, J. Med. Chem., 43, 1533 (2000); H. Nakayama, M. E. Ferreira, A. Rojas de Arias, N. V. de Bilbao, A. Schinini, and A. Fournet, Phytother. Res., 15, 630 (2001); A. Fournet, R. Mahieux, M. A. Fakhfakh, X. Frank, R. Hocquemiller, and B. Frigdère, Bioorg. Med. Chem. Lett., 13, 891 (2003).
52. For biological activities of 2-substituted quinoline derivatives: A. Fournet, A. A. Barrios, V. Munoz, R. Hocquemiller, A. Cavé, and J. Bruneton, Antimicrob. Agents Chemother., 37, 859 (1993); A. Fournet, M. E. Ferreira, A. Rojas de Arias, S. Torres de Ortiz, S. Fuentes, H. Nakayama, and A. Schinini, Antimicrob. Agents Chemother., 40, 2447 (1996); J. C. Gantier, A. Fournet, M. H. Munos, and R. Hocquemiller, Planta Med., 40, 285 (1996); K. Mekouar, J. F. Mouscadet, D. Desmaële, F. Subra, H. Leh, D. Savouré, C. Auclair, and J. d'Angelo, J. Med. Chem., 41, 2846 (1998); F. Zouhiri, J. F. Mouscadet, K. Mekouar, D. Desmaële, D. Savouré, H. Leh, F. Subra, M. Le Bret, C. Auclair, and J. d'Angelo, J. Med. Chem., 43, 1533 (2000); H. Nakayama, M. E. Ferreira, A. Rojas de Arias, N. V. de Bilbao, A. Schinini, and A. Fournet, Phytother. Res., 15, 630 (2001); A. Fournet, R. Mahieux, M. A. Fakhfakh, X. Frank, R. Hocquemiller, and B. Frigdère, Bioorg. Med. Chem. Lett., 13, 891 (2003).
53. For natural occurrence of biologically active quinoline derivatives: A. Fournet, B. Vagnuer, P. Richomme, and J. Bruneton, Can. J. Chem., 67, 2116 (1989); A. Fournet, R. Hocquemiller, F. Roblot, A. Cavé, P. Richomme, and J. Bruneton, J. Nat. Prod., 56, 1547 (1993); J. P. Michael, Nat. Prod. Rep., 12, 465 (1995); M. Balasubramanian and J. G. Kway, "Comprehensive Heterocyclic Chemistry II," ed by A. R. Katritzky, C. W. Rees, and E. F. Scriven, Pergamon Press, Oxford (1996), Vol. 5, Chap. 5.06, p. 245; J. P. Michael, Nat. Prod. Rep., 14, 605 (1997); J. P. Michael, Nat. Prod. Rep., 19, 742 (2002); L. M. Nogle and W. H. Gerwick, J. Nat. Prod., 66, 217 (2003).
54. For natural occurrence of biologically active quinoline derivatives: A. Fournet, B. Vagnuer, P. Richomme, and J. Bruneton, Can. J. Chem., 67, 2116 (1989); A. Fournet, R. Hocquemiller, F. Roblot, A. Cavé, P. Richomme, and J. Bruneton, J. Nat. Prod., 56, 1547 (1993); J. P. Michael, Nat. Prod. Rep., 12, 465 (1995); M. Balasubramanian and J. G. Kway, "Comprehensive Heterocyclic Chemistry II," ed by A. R. Katritzky, C. W. Rees, and E. F. Scriven, Pergamon Press, Oxford (1996), Vol. 5, Chap. 5.06, p. 245; J. P. Michael, Nat. Prod. Rep., 14, 605 (1997); J. P. Michael, Nat. Prod. Rep., 19, 742 (2002); L. M. Nogle and W. H. Gerwick, J. Nat. Prod., 66, 217 (2003).
55. For natural occurrence of biologically active quinoline derivatives: A. Fournet, B. Vagnuer, P. Richomme, and J. Bruneton, Can. J. Chem., 67, 2116 (1989); A. Fournet, R. Hocquemiller, F. Roblot, A. Cavé, P. Richomme, and J. Bruneton, J. Nat. Prod., 56, 1547 (1993); J. P. Michael, Nat. Prod. Rep., 12, 465 (1995); M. Balasubramanian and J. G. Kway, "Comprehensive Heterocyclic Chemistry II," ed by A. R. Katritzky, C. W. Rees, and E. F. Scriven, Pergamon Press, Oxford (1996), Vol. 5, Chap. 5.06, p. 245; J. P. Michael, Nat. Prod. Rep., 14, 605 (1997); J. P. Michael, Nat. Prod. Rep., 19, 742 (2002); L. M. Nogle and W. H. Gerwick, J. Nat. Prod., 66, 217 (2003).
56. For natural occurrence of biologically active quinoline derivatives: A. Fournet, B. Vagnuer, P. Richomme, and J. Bruneton, Can. J. Chem., 67, 2116 (1989); A. Fournet, R. Hocquemiller, F. Roblot, A. Cavé, P. Richomme, and J. Bruneton, J. Nat. Prod., 56, 1547 (1993); J. P. Michael, Nat. Prod. Rep., 12, 465 (1995); M. Balasubramanian and J. G. Kway, "Comprehensive Heterocyclic Chemistry II," ed by A. R. Katritzky, C. W. Rees, and E. F. Scriven, Pergamon Press, Oxford (1996), Vol. 5, Chap. 5.06, p. 245; J. P. Michael, Nat. Prod. Rep., 14, 605 (1997); J. P. Michael, Nat. Prod. Rep., 19, 742 (2002); L. M. Nogle and W. H. Gerwick, J. Nat. Prod., 66, 217 (2003).
57. For natural occurrence of biologically active quinoline derivatives: A. Fournet, B. Vagnuer, P. Richomme, and J. Bruneton, Can. J. Chem., 67, 2116 (1989); A. Fournet, R. Hocquemiller, F. Roblot, A. Cavé, P. Richomme, and J. Bruneton, J. Nat. Prod., 56, 1547 (1993); J. P. Michael, Nat. Prod. Rep., 12, 465 (1995); M. Balasubramanian and J. G. Kway, "Comprehensive Heterocyclic Chemistry II," ed by A. R. Katritzky, C. W. Rees, and E. F. Scriven, Pergamon Press, Oxford (1996), Vol. 5, Chap. 5.06, p. 245; J. P. Michael, Nat. Prod. Rep., 14, 605 (1997); J. P. Michael, Nat. Prod. Rep., 19, 742 (2002); L. M. Nogle and W. H. Gerwick, J. Nat. Prod., 66, 217 (2003).
58. For natural occurrence of biologically active quinoline derivatives: A. Fournet, B. Vagnuer, P. Richomme, and J. Bruneton, Can. J. Chem., 67, 2116 (1989); A. Fournet, R. Hocquemiller, F. Roblot, A. Cavé, P. Richomme, and J. Bruneton, J. Nat. Prod., 56, 1547 (1993); J. P. Michael, Nat. Prod. Rep., 12, 465 (1995); M. Balasubramanian and J. G. Kway, "Comprehensive Heterocyclic Chemistry II," ed by A. R. Katritzky, C. W. Rees, and E. F. Scriven, Pergamon Press, Oxford (1996), Vol. 5, Chap. 5.06, p. 245; J. P. Michael, Nat. Prod. Rep., 14, 605 (1997); J. P. Michael, Nat. Prod. Rep., 19, 742 (2002); L. M. Nogle and W. H. Gerwick, J. Nat. Prod., 66, 217 (2003).
59. For natural occurrence of biologically active quinoline derivatives: A. Fournet, B. Vagnuer, P. Richomme, and J. Bruneton, Can. J. Chem., 67, 2116 (1989); A. Fournet, R. Hocquemiller, F. Roblot, A. Cavé, P. Richomme, and J. Bruneton, J. Nat. Prod., 56, 1547 (1993); J. P. Michael, Nat. Prod. Rep., 12, 465 (1995); M. Balasubramanian and J. G. Kway, "Comprehensive Heterocyclic Chemistry II," ed by A. R. Katritzky, C. W. Rees, and E. F. Scriven, Pergamon Press, Oxford (1996), Vol. 5, Chap. 5.06, p. 245; J. P. Michael, Nat. Prod. Rep., 14, 605 (1997); J. P. Michael, Nat. Prod. Rep., 19, 742 (2002); L. M. Nogle and W. H. Gerwick, J. Nat. Prod., 66, 217 (2003).
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