Reaction of pyridazine and quinoline with silyl enol ethers in the presence of alkyl chloroformate

Heterocycles

Volumn 46, Issue 1, 1997, Pages 83-86

  Itoh, Takashi ^a   Miyazaki, Michiko ^a   Nagata, Kazuhiro ^a   Ohsawa, Akio ^a  

^a SHOWA UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0002603870     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-97-s29     Document Type: Article

References (14)

1. E. W. Colvin, "Silicon Reagents in Organic Synthesis," Academic Press, New York, 1988.
2. C. Gennari in "Comprehensive Organic Synthesis," ed. by B. M. Trost and I. Fleming, vol.ed. by C. H. Heathcock, Pergamon Press, Oxford, 1991, Vol. 2, pp. 629-660.
3. a) The application toward 5-membered azaaromatics has been reported; see, T. Itoh, M. Miyazaki, H. Hasegawa, K. Nagata, and A. Ohsawa, Chem. Commun., 1996, 1217.
4. b) Highly π-electron deficient 1,2,3-triazines are found to be the substrates for the reaction with silyl enol ethers; see, T. Itoh, Y. Matsuya, H. Hasegawa, K. Nagata, M. Okada, and A. Ohsawa, J. Chem. Soc., Perkin Trans. 1, 1996, 2511.
5. a) K. Akiba, Y. Nishihara, and M. Wada, Tetrahedron Lett., 1983, 24, 5269.
6. b) M. Wada, Y. Nishihara, and K. Akiba, Tetrahedron Lett., 1985, 26, 3267.
7. Y. Yamamoto, A. Sakaguchi, H. Yoshida, and K. Akiba, J. Chem. Soc., Perkin Trans. 1, 1988, 725.
8. 2=H). Thus, unsubstituted adducts could be prepared regioselectively at γ-position when this type of silyl enolate was used for pyridine.
9. a) T. Itoh, H. Hasegawa, K. Nagata, and A. Ohsawa, J. Org. Chem., 1994, 59, 1319.
10. b) T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya, M. Okada, and A. Ohsawa, Chem. Pharm. Bull., 1994, 42, 1768.
11. c) T. Itoh, H. Hasegawa, K. Nagata, M. Okada, and A. Ohsawa, Tetrahedron, 1994, 50, 13089.
12. 1H-NMR experiment, probably due to the low concentration of it.
13. 1H-NMR experiment suggested that less than 5% of quinoline was quaternized in the reaction mixture.
14. Akiba et al. reported similar results in a communication; see, K. Akiba, T. Kobayashi, and Y. Yamamoto, Heterocycles, 1984, 22, 1519.