New synthesis of isoquinoline derivatives by reactions of 2-(2-methoxyethenyl)benzonitriles with organolithiums and lithium dialkylamides

Chemistry Letters

Volumn 33, Issue 3, 2004, Pages 236-237

  Kobayashi, Kazuhiro ^a   Shiokawa, Taiyo ^a   Morikawa, Osamu ^a   Konishi, Hisatoshi ^a  

^a TOTTORI UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ALKYL GROUP; AMIDE; AMINE; BENZONITRILE; CARBON; ISOQUINOLINE DERIVATIVE; LITHIUM DERIVATIVE; NITRILE; ORGANOLITHIUM COMPOUND; POLYCYCLIC AROMATIC HYDROCARBON DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; MOLECULE; SYNTHESIS; TEMPERATURE;

EID: 2442682793     PISSN: 03667022     EISSN: None     Source Type: Journal    
DOI: 10.1246/cl.2004.236     Document Type: Article

References (45)

1. K. Kobayashi, K. Yoneda, M. Mano, O. Morikawa, and H. Konishi, Chem. Lett., 32, 76 (2003).
2. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
3. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
4. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
5. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
6. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
7. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
8. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
9. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
10. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
11. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
12. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
13. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
14. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
15. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
16. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
17. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
18. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
19. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
20. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
21. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
22. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
23. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
24. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
25. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
26. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R. C. Larock, Org. Lett., 3, 2973 (2001); G. X. Dai and R. C. Larock, Org. Lett., 3, 4035 (2001); P. J. Campos, M. Caro, and M. A. Rodríguez, Tetrahedron Lett., 42, 3575 (2001); K. R. Roesch, H. M. Zhang, and R. C. Larock, J. Org. Chem., 66, 8042 (2001); A. S. Capilla, M. Romero, M. D. Pujol, D. H. Caignard, and P. Renard, Tetrahedron, 57, 8297 (2001); K. R. Roesch and R. C. Larock, J. Org. Chem., 67, 86 (2002); G. X. Dai and R. C. Larock, Org. Lett., 4, 193 (2002); W. M. Abdou, A. F. M. Fahmy, and A. A.-A. Kamel, Eur. J. Org. Chem., 2002, 1696; Q. H. Huang, J. A. Hunter, and R. C. Larock, J. Org. Chem., 67, 3437 (2002); Q. H. Huang and R. C. Larock, Tetrahedron Lett., 43, 3557 (2002); S. K. Chattopadhyay, S. Maity, B. K. Pal, and S. Panja, Tetrahedron Lett., 43, 5079 (2002); G. X. Dai and R. C. Larock, J. Org. Chem., 67, 7042 (2002); T. V. V. Ramakrishna and P. R. Sharp, Org. Lett., 5, 877 (2003); B. Pal, P. Jaisankar, and V. S. Giri, Synth. Commun., 33, 2339 (2003); S. G. Lim, J. H. Lee, C. W. Moon, J. B. Hong, and C. H. Jun, Org. Lett., 5, 2759 (2003) and refs cited therein. After the completion of the present work we became aware of a publication by Ichikawa and colleagues who report a synthesis of 1,4-disubstituted 3-fluoroisoquinolines by reactions of o-cyano-β,β- difluorostyrenes with organometals; J. Ichikawa, Y. Wada, H. Miyazaki, T. Mori, and H. Kuroki, Org. Lett., 5, 1455 (2003); For recent utilizations of isoquinolines for the preparation of isoquinoline alkaloides: H. Kohno and K. Yamada, Heterocycles, 51, 103 (1999); K. Orito, Y. Satoh, H. Nishizawa, and M. Tokuda, Org. Lett., 2, 2535 (2000).
27. For an excellent review for earlier works on the synthesis of isoquinolines: T. Kametani and K, Fukumoto, in "The Chemistry of Heterocyclic Compounds, Isoquinolines," ed. by G. Grethe, Wiley, New York (1981), Vol. 38, Part 1, Chap. 2, p 139; For recent reports: E. M. Brun, S. Gil, R. Mestres, and M. Parra, Synthesis, 2000, 273; A. A. Fadda and H. M. Refat, Synth. Commun., 30, 341 (2000); T. Sakamoto, A. Numata, and Y. Kondo, Chem. Pharm. Bull., 48, 669 (2000); R. Fujita, M. Hoshino, H. Tomisawa, and H. Hongo, Chem. Pharm. Bull., 48, 1814 (2000); H. Ishii, Y. Imai, T. Hirano, S. Maki, H. Niwa, and M. Ohashi, Tetrahedron Lett., 41, 6467 (2000); H. Tsutsui and K. Narasaka, Chem. Lett., 2001, 526; M. A. A. Meziane, S, Royer, and J. P. Bazureau, Tetrahedron Lett., 42, 1017 (2001); Q. H. Huang, J. A. Hunter, and R.
28. For reports on the synthesis and biological importance of isoquinolin-1-amines: T. Saito, T. Ohkubo, H. Kuboki, M. Maeda, K. Tsuda, T. Karakasa, and S. Satsumabayashi, J. Chem. Soc., Perkin Trans. 1, 1998, 3065; J. B. M. Rewinkel, H. Lucas, M. J. Smit, A. B. J. Noach, T. G. van Dinther, A. M. M. Rood, A. J. S. M. Jenneboer, and C. A. A. van Boeckel, Bioorg. Med. Chem. Lett., 9, 2837 (1999); J. D. Tovar and T. M. Swager, J. Org. Chem., 64, 6499 (1999).
29. For reports on the synthesis and biological importance of isoquinolin-1-amines: T. Saito, T. Ohkubo, H. Kuboki, M. Maeda, K. Tsuda, T. Karakasa, and S. Satsumabayashi, J. Chem. Soc., Perkin Trans. 1, 1998, 3065; J. B. M. Rewinkel, H. Lucas, M. J. Smit, A. B. J. Noach, T. G. van Dinther, A. M. M. Rood, A. J. S. M. Jenneboer, and C. A. A. van Boeckel, Bioorg. Med. Chem. Lett., 9, 2837 (1999); J. D. Tovar and T. M. Swager, J. Org. Chem., 64, 6499 (1999).
30. For reports on the synthesis and biological importance of isoquinolin-1-amines: T. Saito, T. Ohkubo, H. Kuboki, M. Maeda, K. Tsuda, T. Karakasa, and S. Satsumabayashi, J. Chem. Soc., Perkin Trans. 1, 1998, 3065; J. B. M. Rewinkel, H. Lucas, M. J. Smit, A. B. J. Noach, T. G. van Dinther, A. M. M. Rood, A. J. S. M. Jenneboer, and C. A. A. van Boeckel, Bioorg. Med. Chem. Lett., 9, 2837 (1999); J. D. Tovar and T. M. Swager, J. Org. Chem., 64, 6499 (1999).
31. J. A. Joule, K. Mills, G. F. Smith, "Heterocyclic Chemistry, 3rd ed.," Stanley Thrones, London (1995), Chap. 6, p 120; K. S. Chen, F. N. Ko, C. M. Teng, and Y. C. Wu, J. Nat. Prod., 59, 531 (1996); Y. Yoshida, D. Barrett, H. Azami, C. Morinaga, S. Matsumoto, Y. Matsumoto, and H. Takasugi, Bioorg. Med. Chem., 7, 2647 (1999); Q. Chao, L. Deng, H. C. Shih, L. M. Leoni, D. Genini, D. A. Carson, and H. B. Cottam, J. Med. Chem., 42, 3860 (1999); J. E. Van Muijlwijk-Koezen, H. Timmerman, H. Van der Goot, W. M. P. B. Menge, J. F. Von Kuenzel, M. De Groote, and A. P. Ijzerman, J. Med. Chem., 43, 2227 (2000); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chiaroni, P. Ducrot, E. Bisagni, L. Jun, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000); R. Y. Kuo, F. R. Chang, C. C. Wu, R. Patnam, W. Y. Wang, Y. C. Du, and Y. C. Wu, Bioorg. Med. Chem. Lett., 13, 2789 (2003).
32. J. A. Joule, K. Mills, G. F. Smith, "Heterocyclic Chemistry, 3rd ed.," Stanley Thrones, London (1995), Chap. 6, p 120; K. S. Chen, F. N. Ko, C. M. Teng, and Y. C. Wu, J. Nat. Prod., 59, 531 (1996); Y. Yoshida, D. Barrett, H. Azami, C. Morinaga, S. Matsumoto, Y. Matsumoto, and H. Takasugi, Bioorg. Med. Chem., 7, 2647 (1999); Q. Chao, L. Deng, H. C. Shih, L. M. Leoni, D. Genini, D. A. Carson, and H. B. Cottam, J. Med. Chem., 42, 3860 (1999); J. E. Van Muijlwijk-Koezen, H. Timmerman, H. Van der Goot, W. M. P. B. Menge, J. F. Von Kuenzel, M. De Groote, and A. P. Ijzerman, J. Med. Chem., 43, 2227 (2000); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chiaroni, P. Ducrot, E. Bisagni, L. Jun, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000); R. Y. Kuo, F. R. Chang, C. C. Wu, R. Patnam, W. Y. Wang, Y. C. Du, and Y. C. Wu, Bioorg. Med. Chem. Lett., 13, 2789 (2003).
33. J. A. Joule, K. Mills, G. F. Smith, "Heterocyclic Chemistry, 3rd ed.," Stanley Thrones, London (1995), Chap. 6, p 120; K. S. Chen, F. N. Ko, C. M. Teng, and Y. C. Wu, J. Nat. Prod., 59, 531 (1996); Y. Yoshida, D. Barrett, H. Azami, C. Morinaga, S. Matsumoto, Y. Matsumoto, and H. Takasugi, Bioorg. Med. Chem., 7, 2647 (1999); Q. Chao, L. Deng, H. C. Shih, L. M. Leoni, D. Genini, D. A. Carson, and H. B. Cottam, J. Med. Chem., 42, 3860 (1999); J. E. Van Muijlwijk-Koezen, H. Timmerman, H. Van der Goot, W. M. P. B. Menge, J. F. Von Kuenzel, M. De Groote, and A. P. Ijzerman, J. Med. Chem., 43, 2227 (2000); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chiaroni, P. Ducrot, E. Bisagni, L. Jun, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000); R. Y. Kuo, F. R. Chang, C. C. Wu, R. Patnam, W. Y. Wang, Y. C. Du, and Y. C. Wu, Bioorg. Med. Chem. Lett., 13, 2789 (2003).
34. J. A. Joule, K. Mills, G. F. Smith, "Heterocyclic Chemistry, 3rd ed.," Stanley Thrones, London (1995), Chap. 6, p 120; K. S. Chen, F. N. Ko, C. M. Teng, and Y. C. Wu, J. Nat. Prod., 59, 531 (1996); Y. Yoshida, D. Barrett, H. Azami, C. Morinaga, S. Matsumoto, Y. Matsumoto, and H. Takasugi, Bioorg. Med. Chem., 7, 2647 (1999); Q. Chao, L. Deng, H. C. Shih, L. M. Leoni, D. Genini, D. A. Carson, and H. B. Cottam, J. Med. Chem., 42, 3860 (1999); J. E. Van Muijlwijk-Koezen, H. Timmerman, H. Van der Goot, W. M. P. B. Menge, J. F. Von Kuenzel, M. De Groote, and A. P. Ijzerman, J. Med. Chem., 43, 2227 (2000); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chiaroni, P. Ducrot, E. Bisagni, L. Jun, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000); R. Y. Kuo, F. R. Chang, C. C. Wu, R. Patnam, W. Y. Wang, Y. C. Du, and Y. C. Wu, Bioorg. Med. Chem. Lett., 13, 2789 (2003).
35. J. A. Joule, K. Mills, G. F. Smith, "Heterocyclic Chemistry, 3rd ed.," Stanley Thrones, London (1995), Chap. 6, p 120; K. S. Chen, F. N. Ko, C. M. Teng, and Y. C. Wu, J. Nat. Prod., 59, 531 (1996); Y. Yoshida, D. Barrett, H. Azami, C. Morinaga, S. Matsumoto, Y. Matsumoto, and H. Takasugi, Bioorg. Med. Chem., 7, 2647 (1999); Q. Chao, L. Deng, H. C. Shih, L. M. Leoni, D. Genini, D. A. Carson, and H. B. Cottam, J. Med. Chem., 42, 3860 (1999); J. E. Van Muijlwijk-Koezen, H. Timmerman, H. Van der Goot, W. M. P. B. Menge, J. F. Von Kuenzel, M. De Groote, and A. P. Ijzerman, J. Med. Chem., 43, 2227 (2000); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chiaroni, P. Ducrot, E. Bisagni, L. Jun, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000); R. Y. Kuo, F. R. Chang, C. C. Wu, R. Patnam, W. Y. Wang, Y. C. Du, and Y. C. Wu, Bioorg. Med. Chem. Lett., 13, 2789 (2003).
36. J. A. Joule, K. Mills, G. F. Smith, "Heterocyclic Chemistry, 3rd ed.," Stanley Thrones, London (1995), Chap. 6, p 120; K. S. Chen, F. N. Ko, C. M. Teng, and Y. C. Wu, J. Nat. Prod., 59, 531 (1996); Y. Yoshida, D. Barrett, H. Azami, C. Morinaga, S. Matsumoto, Y. Matsumoto, and H. Takasugi, Bioorg. Med. Chem., 7, 2647 (1999); Q. Chao, L. Deng, H. C. Shih, L. M. Leoni, D. Genini, D. A. Carson, and H. B. Cottam, J. Med. Chem., 42, 3860 (1999); J. E. Van Muijlwijk-Koezen, H. Timmerman, H. Van der Goot, W. M. P. B. Menge, J. F. Von Kuenzel, M. De Groote, and A. P. Ijzerman, J. Med. Chem., 43, 2227 (2000); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chiaroni, P. Ducrot, E. Bisagni, L. Jun, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000); R. Y. Kuo, F. R. Chang, C. C. Wu, R. Patnam, W. Y. Wang, Y. C. Du, and Y. C. Wu, Bioorg. Med. Chem. Lett., 13, 2789 (2003).
37. J. A. Joule, K. Mills, G. F. Smith, "Heterocyclic Chemistry, 3rd ed.," Stanley Thrones, London (1995), Chap. 6, p 120; K. S. Chen, F. N. Ko, C. M. Teng, and Y. C. Wu, J. Nat. Prod., 59, 531 (1996); Y. Yoshida, D. Barrett, H. Azami, C. Morinaga, S. Matsumoto, Y. Matsumoto, and H. Takasugi, Bioorg. Med. Chem., 7, 2647 (1999); Q. Chao, L. Deng, H. C. Shih, L. M. Leoni, D. Genini, D. A. Carson, and H. B. Cottam, J. Med. Chem., 42, 3860 (1999); J. E. Van Muijlwijk-Koezen, H. Timmerman, H. Van der Goot, W. M. P. B. Menge, J. F. Von Kuenzel, M. De Groote, and A. P. Ijzerman, J. Med. Chem., 43, 2227 (2000); M. Croisy-Delcey, A. Croisy, D. Carrez, C. Huel, A. Chiaroni, P. Ducrot, E. Bisagni, L. Jun, and G. Leclercq, Bioorg. Med. Chem., 8, 2629 (2000); R. Y. Kuo, F. R. Chang, C. C. Wu, R. Patnam, W. Y. Wang, Y. C. Du, and Y. C. Wu, Bioorg. Med. Chem. Lett., 13, 2789 (2003).
38. R. D. Rieke, D. E. Stack, B. T. Dawson, and T.-C. Wu, J. Org. Chem., 58, 2483 (1993).
39. J. H. Helberger and A. von Rebay, Liebigs Ann. Chem., 531, 279 (1937).
40. V. J. Bauer, B. J. Duffy, D. Hoffman, S. S. Kloize, R. W. Kosely, Jr., A. R. McFadden, L. L. Martin, H. H. Ong, and H. M. Geyer, J. Med. Chem., 19, 1315 (1976).
41. L. Friedman and H. Shechter, J. Org. Chem., 26, 2522 (1961).
42. The use of less than 2 equiv. of organolithiums resulted in decrease of the yields of the desired products and the starting material 1a was recovered.
43. f 0.71 (5:1 hexane-AcOEt); 3c: mp 104°C; 3d: mp 120-121°C; 3e: mp 133-134°C; 3f: mp 151-152°C; 3g: mp 136-137°C.
44. W. Krabbe, H. H. Böhlk, and K. Heinz, Ber., 71, 64 (1938).
45. K. Ziegler and H. Zeiser, Liebigs Ann. Chem., 485, 174 (1931).