Generation of polysubstituted 2-pyridinecarboxylic acid derivatives from the reaction of (functionalised) 2-oxa-5-azabicyclo[2.2.2]oct-5-en-3-ones with various nucleophiles

Tetrahedron

Volumn 52, Issue 38, 1996, Pages 12529-12540

  Dubois, Kristof J ^a   Fannes, Christine C ^a   Toppet, Suzanne M ^a   Hoornaert, Georges J ^a  

^a UNIVERSITY OF LEUVEN   (Belgium)

Author keywords

[No Author keywords available]

Indexed keywords

PICOLINIC ACID DERIVATIVE; PYRIDINE DERIVATIVE;

ARTICLE; DRUG SYNTHESIS; PRIORITY JOURNAL; REACTION ANALYSIS;

EID: 0030590524     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4020(96)00733-8     Document Type: Article

References (24)

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6. 4. See, for recent examples : Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924). Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc., 1991, 113, 1713.
7. 4. See, for recent examples : Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924). Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc., 1991, 113, 1713.
8. 4. See, for recent examples : Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924). Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc., 1991, 113, 1713.
9. 4. See, for recent examples : Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924). Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc., 1991, 113, 1713.
10. 4. See, for recent examples : Makino, E.; Iwasaki, N.; Yagi, N.; Ohashi, T.; Kato, H.; Ito, Y.; Azuma, H. Chem. Pharm. Bull. 1990, 38, 201-207. Foster, C.J.; Gilkerson, T.; Stocker, R. European Patent # 447,004 (Chem. Abstr. 1992, 116, 128668e). Finkelstein, B.L., US Patent # 794,554 (Chem. Abstr. 1993, 119, 160130w). Takasugi, H.; Kuno, A.; Sakai, H. European Patent # 387,070 (Chem. Abstr. 1991, 114, P101743x). Takabe, F.; Saito, Y.; Tamaru, M.; Tachikawa, S.; Yoshida, R. Japanese Patent # 06,316,574 (Chem. Abstr. 1995, 122, 160668e). Kleemann, A.; Graef, H. British Patent # 2,277,930 (Chem. Abstr. 1995, 122, 105924). Boger, D. L.; Corbett, W. L.; Curran, T. T.; Kasper, A. M. J. Am. Chem. Soc., 1991, 113, 1713.
11. 5. Methods for the synthesis of 5,6-disubstituted-2-pyridinecarboxylic acid derivatives. See for examples: Molina, P.; Allere, E.; Angeles Lorenzo, M. Synthesis 1993, 1239; Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc. Perkin Trans I 1990, 2193, Warawa, E.J. J. Org. Chem. 1975, 40, 2092; Neunhoeffer, H.; Werner, G. Liebigs Ann. Chem. 1973, 437; Sagi, M.; Amano, M.; Kohno, S.; Yamanaka, H. Heterocycles 1989, 29, 2249.
12. 5. Methods for the synthesis of 5,6-disubstituted-2-pyridinecarboxylic acid derivatives. See for examples: Molina, P.; Allere, E.; Angeles Lorenzo, M. Synthesis 1993, 1239; Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc. Perkin Trans I 1990, 2193, Warawa, E.J. J. Org. Chem. 1975, 40, 2092; Neunhoeffer, H.; Werner, G. Liebigs Ann. Chem. 1973, 437; Sagi, M.; Amano, M.; Kohno, S.; Yamanaka, H. Heterocycles 1989, 29, 2249.
13. 5. Methods for the synthesis of 5,6-disubstituted-2-pyridinecarboxylic acid derivatives. See for examples: Molina, P.; Allere, E.; Angeles Lorenzo, M. Synthesis 1993, 1239; Barluenga, J.; Ferrero, M.; Palacios, F. J. Chem. Soc. Perkin Trans I 1990, 2193, Warawa, E.J. J. Org. Chem. 1975, 40, 2092; Neunhoeffer, H.; Werner, G. Liebigs Ann. Chem. 1973, 437; Sagi, M.; Amano, M.; Kohno, S.; Yamanaka, H. Heterocycles 1989, 29, 2249.
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