A convenient one-pot synthesis of 6-trifluoromethyl-pyridines

Heterocycles

Volumn 48, Issue 4, 1998, Pages 779-785

  Katsuyama, Isamu ^a   Ogawa, Seiya ^a   Nakamura, Hiroko ^a   Yamaguchi, Yoshihiro ^a   Funabiki, Kazumasa ^a   Matsui, Masaki ^a   Muramatsu, Hiroshige ^a   Shibata, Katsuyoshi ^a  

^a GIFU UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0000376885     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-8102     Document Type: Article

References (24)

1. S. J. Gould and S. M. Weinreb, Fortschr. Chem. Org. Naturst., 1982, 41, 77 ;
2. D. M. Balitz, J. A. Bush, W. T. Bradner, T. W. Doyle, F. A. O'Herron, and D. E. Nettleton, J. Antibiot., 1982, 35, 259.
3. S. Kawamura, T. Hamada, R. Sato, and Y. Sanemitsu, J. Agric. Food Chem., 1991, 39, 2279.
4. S. Kagabu and H. Matsumoto, J. Agric. Food Chem., 1997, 45, 276.
5. S. G. Hegde and M. D. Mahoney, J. Agric. Food Chem., 1993, 41, 2131.
6. G. Grethe and T. Mitt, Ger. Pat., 1 806 909, 1978 (Chem. Abstr., 1979, 90, 22838q).
7. I. Katsuyama, S. Ogawa, Y. Yamaguchi, K. Funabiki, M. Matsui, H. Muramatsu, and K. Shibata, Synthesis, 1997, 1321.
8. S. Kawamura, J. Sato, T. Hamada, M. Sakaki, and Y. Sanemitsu, J. Agric. Food Chem., 1993, 41, 288.
9. L. F. Lee and J. E. Normansell, J. Org. Chem., 1990, 55, 2964;
10. W. F. Goure, J. Heterocycl. Chem., 1993, 30, 71;
11. F. Evariste, Z. Janousek, C. Maliverney, R. Merenyi, and H. G. Viehe, J. Pract. Chem., 1993,335, 35.
12. A convenient method has been reported using highly reactive enaminonitriles in M. T. Cocco, C. Congiu, and V. Onnis, J. Heterocycl. Chem., 1995, 32, 543. In contrast, the reaction using less reactive enamines (2) afforded both the desired (5) and the isomeric pyridines (6) in low yields.
13. K. Shibata, K. Urano, and M. Matsui, Bull. Chem. Soc. Jpn. 1988, 61, 2199;
14. K. Shibata, I. Katsuyama, M. Matsui, and H. Muramatsu, Ibid., 1990, 63, 3710;
15. Idem, J. Heterocycl. Chem., 1991, 28, 161.
16. I. Katsuyama, K. Funabiki, M. Matsui, H. Muramatsu, and K. Shibata, Tetrahedron Lett., 1996, 37, 4117.
17. P. Cozzi, G. Carganico, D. Fusar, M. Grossoni, M. Menichincheri, V. Pinciroli, R. Tanani, F. Vaghi, and P. Salvati, J. Med. Chem., 1993,36, 2964.
18. K. Meguro, M. Aizawa, T. Sohda, Y. Kawamatsu, and A. Nagaoka, Chem. Pharm. Bull., 1985, 33, 3787;
19. A. Kuno, Y. Sugiyama, K. Katsuta, T. Kamitani, and H. Takasugi, Chem. Pharm. Bull., 1992, 40, 1452.
20. A. Kuno, H. Sakai, Y. Sugiyama, and H. Takasugi, Chem. Pharm. Bull., 1993, 41, 156 ;
21. A. Kuno, H. Sakai, M. Ohkubo, and H. Takasugi, Ibid., 1993,41, 163.
22. B. Loev and K. M. Snader, J. Org. Chem., 1965, 30, 1914;
23. U. Eisner and J. Kuthan, Chem. Rev., 1972, 72, 1.
24. D. Mead, R. Loh, A. E. Asato, and R. S. H. Liu, Tetrahedron Lett., 1985, 26, 2873.