A new entry to the synthesis of 5-substituted 1,2,3-triazines by reaction with silyl enol ethers and ceric ammonium nitrate

Journal of the Chemical Society - Perkin Transactions 1

Volumn , Issue 20, 1996, Pages 2511-2515

  Itoh, Takashi ^a   Matsuya, Yûji ^a   Hasegawa, Hiroshi ^a,b   Nagata, Kazuhiro ^a   Okada, Mamiko ^a   Ohsawa, Akio ^a  

^a SHOWA UNIVERSITY   (Japan)

^b SSP CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 33748964633     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/p19960002511     Document Type: Article

References (29)

1. (a) H. Neunhoeffer in Comprehensive Heterocyclic Chemistry, series eds. A. R. Katritzky and C. W. Rees, Vol. eds. A. J. Boulton and A. McKillop, Pergamon Press, Oxford, 1984, vol. 3, pp. 369-384;
2. (b) A. Ohsawa, H. Arai, H. Ohnishi, T. Itoh, T. Kaihoh, M. Okada and H. Igeta, J. Org. Chem., 1985, 50, 5520;
3. (c) H. Neunhoeffer, M. Clausen, H.-D. Vötter, H. Ohl, C. Krüger and K. Angermund, Liebigs Ann. Chem., 1985, 1732.
4. (a) A. Ohsawa, T. Kaihoh and H. Igeta, J. Chem. Soc., Chem. Commun., 1985, 1370;
5. (b) T. Itoh, M. Okada, K. Nagata and A. Ohsawa, Heterocycles, 1992, 34, 1183.
6. T. Itoh, K. Nagata, T. Kaihoh, M. Okada, C. Kawabata, H. Arai, H. Ohnishi, K. Yamaguchi, H. Igeta, A. Ohsawa and Y. Iitaka, Heterocycles, 1992, 33, 631.
7. For example, a 5-halogenotriazine reacted with hydroxide ion at the C-4 position, and a 5-hydroxy derivative was obtained only by the reaction with superoxide anion. See, (a) T. Itoh, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron Lett., 1990, 31, 2429;
8. (b) T. Itoh, K. Nagata, M. Okada, H. Takahashi and A. Ohsawa, Tetrahedron, 1991, 47, 4317.
9. O. N. Chupakhin, V. N. Charushin and H. C. van der Plas, Tetrahedron, 1988, 44, 1.
10. H. Neunhoeffer, R. Bopp and W. Diehl, Liebigs Ann. Chem., 1993, 367.
11. T. Itoh, K. Nagata, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1993, 40, 2283.
12. When 1 was treated with various electrophiles, the reaction occurred exclusively at the N-2 position. A. Ohsawa, T. Itoh, K. Yamaguchi and C. Kawabata, Chem. Pharm. Bull., 1991, 39, 2117.
13. (a) K. Nagata, T. Itoh, M. Okada, H. Takahashi and A. Ohsawa, Heterocycles, 1991, 32, 855;
14. (b) K. Nagata, T. Itoh, M. Okada, H. Takahashi and A. Ohsawa, Heterocycles, 1991, 32, 2015.
15. (a) T. Itoh, K. Nagata, M. Okada and A. Ohsawa, Heterocycles, 1993, 35, 581;
16. (b) K. Nagata, T. Itoh, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1993, 41, 1644;
17. (c) T. Itoh, Y. Matsuya, K. Nagata, M. Okada and A. Ohsawa, J. Chem. Soc., Chem. Commun., 1995, 2067.
18. Akiba et al. reported that silyl enol ethers reacted with N-alkoxycarbonylpyridinium salts to give 1,4-dihydro adducts. See, (a) K. Akiba, Y. Nishihara and M. Wada, Tetrahedron Lett., 1983, 24, 5269;
19. (b) M. Wada, Y. Nishihara and K. Akiba, Tetrahedron Lett., 1985, 26, 3267. The application of this reaction system to five-membered azaaromatics was recently performed by our group;
20. (c) T. Itoh, M. Miyazaki, H. Hasegawa, K. Nagata and A. Ohsawa, Chem. Commun., 1996, 1217.
21. Preliminary communication; T. Itoh, Y. Matsuya, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1995, 43, 881.
22. In the cases of the 5-oxofuryl derivatives (Table 1, entries 9-12), the lactone ring was labile under the reaction conditions, and decomposed without formation of the aromatized compound 4.
23. Only 3% of the product 7a and 7% of the 5-desubstituted triazine 1a were isolated from the reaction mixture.
24. The use of unstable quaternary salts of azaaromatics other than 1,2,3-triazines was reported by us using allyl(tributyl)tin and bis(tributylstannyl)acetylene as nucleophiles. See, (a) T. Itoh, H. Hasegawa, K. Nagata and A. Ohsawa, J. Org. Chem., 1994, 59, 1319;
25. (b) T. Itoh, H. Hasegawa, K. Nagata, Y. Matsuya, M. Okada and A. Ohsawa, Chem. Pharm. Bull., 1994, 42, 1768;
26. (c) T. Itoh, H. Hasegawa, K. Nagata, M. Okada and A. Ohsawa, Tetrahedron, 1994, 50, 13089.
27. T. H. Chan in Comprehensive Organic Synthesis, ed. C. H. Heathcock, Pergamon Press, Oxford, 1991, vol. 2, p. 595, and references cited therein.
28. Allyltributyltin was shown to react with 1,2,3-triazines in the presence of 1-chloroethyl chloroformate to give 2,5-dihydro adducts in a similar manner. The results will be published later.
29. A. Ohsawa, H. Arai, H. Ohnishi, T. Kaihoh, T. Itoh, K. Yamaguchi, H. Igeta and Y. Iitaka, Yakugaku Zasshi, 1985, 105, 1122.