Pyrimidine Derivatives and Related Compounds. XLVI.1) Thermal and Photochemical Transformation of 5-Substituted 6-Azido-1,3-dimethyluracils into Fused Pyrimidines such as Isoxazolo[3,4-d]pyrimidines, Pyrazolo[3,4-d]-pyrimidines, and Pyrimido[4,5-d]-[1,2,3]triazine

Chemical and Pharmaceutical Bulletin

Volumn 31, Issue 11, 1983, Pages 3959-3966

  Hirota, Kosaku ^a   Maruhashi, Kazuo ^a   Asao, Tetsuji ^a   Kitamura, Norihiko ^a   Maki, Yoshifumi ^a   Senda, Shigeo ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

6 azido 5 formyl 1,3 dimethyluracil; azido group; isoxazolo 3,4 d pyrimidine; photolysis; pyrazolo 3,4 d pyrimidine; pyrimido 4,5 b indole; pyrimido 4,5 b quinoline; pyrimido 4,5 d 1,2,3 triazine; thermolysis

Indexed keywords

EID: 85008137539     PISSN: 00092363     EISSN: 13475223     Source Type: Journal    
DOI: 10.1248/cpb.31.3959     Document Type: Article

References (30)

1. K. Hirota, Y. Kitade, K. Shimada, S. Senda, and Y. Maki, J. Chem. Soc., Perkin Trans. 1, 1983, 1293.
2. S. Patai (ed.), “The Chemistry of the Azido Group,” Wiley-Interscience, New York, 1971.
3. E. F. V. Scriven, “Reactive Intermediates,” Vol. 2, ed. by R. A. Abramovitch, Plenum Press, New York, 1982, pp. 1—54.
4. F. Yoneda and Y. Sakuma, J. Heterocycl. Chem., 10, 993 (1973).
5. S. Senda, K. Hirota, T. Asao, and K. Maruhashi, J. Am. Chem. Soc., 99, 7358 (1977)
6. S. Senda, K. Hirota, T. Asao, and K. Maruhashi, J. Am. Chem. Soc., 100, 7661 (1978).
7. R. Marumoto and Y. Furukawa, Chem. Pharm. Bull., 25, 2974, (1977)
8. S. Nishigaki, Y. Kanamori, and K. Senga, Chem. Pharm. Bull., 26, 2497 (1978)
9. K. Hirota, T. Asao, T. Fujioka, and S. Senda, Nippon Kagaku Kaishi, 1981, 721.
10. A. G. Rowley, “Organophosphorus Reagents in Organic Synthesis,” ed. by J. I. G. Cadogan, Academic Press, London, 1979, pp. 295—350.
11. No literature on the synthesis of a pyrimido[4,5-d] [1, 2, 3]triazine ring system has been found in Chem. Abstr.; see an excellent review of 1,2,3-triazines: R. J. Kobylecki, “Advances in Heterocyclic Chemistry,” Vol. 19, ed. by A. R. Katritzky and A. J. Boulton, Academic Press, New York, 1976, pp. 215—278.
12. B. M. Adger, S. Bradbury, M. Keating, C. W. Rees, R. C. Storr, and M. T. Williams, J. Chem. Soc., Perkin Trans. 1, 1975, 31.
13. W. Pfleiderer and G. Strauss, Justus Liebigs Ann. Chem., 612, 173 (1958).
14. F. Yoneda, T. Yano, and M. Higuchi, Chem. Lett., 1979, 155.
15. K. Senga, K. Shimizu, S. Nishigaki, and F. Yoneda, Heterocycles, 6, 1361 (1977)
16. F. Yoneda, F. Takayama, and A. Koshiro, Chem. Pharm. Bull., 27, 2507 (1979)
17. Y. Tominaga, H. Okuda, M. Tochiki, Y. Matsuda, and G. Kobayashi, Heterocycles, 15, 679 (1981).
18. W. Pfleiderer and K.-H. Schundehutte, Justus Liebigs Ann. Chem., 615, 42 (1958)
19. P. Schmidt, K. Eichenberger, and J. Druey, Helv. Chim. Acta, 41, 1052 (1958)
20. S. Senda, K. Hirota, and G.-N. Yang, Chem. Pharm. Bull., 20, 391 (1972)
21. S. Senda, K. Hirota, and G.-N. Yang, Chem. Pharm. Bull., 20, 399 (1972).
22. S. Senda, K. Hirota, and M. Takahashi, J. Chem. Soc., Perkin Trans. 1, 1975, 503.
23. J. M. Lindley, I. M. McRobbie, O. Meth-Cohn, and H. Suschitzky, J. Chem. Soc., Perkin Trans. 1, 1977, 2194.
24. L. K. Dyall and J. E. Kemp, J. Chem. Soc., (B), 1968, 976
25. L. K. Dyall, Aust. J. Chem., 30, 2669 (1977).
26. L. Krbechek and H. Takimoto, J. Org. Chem., 33, 4286 (1968)
27. G. R. Cliff and G. Jones, J. Chem. Soc., Chem. Commun., 1970, 1705.
28. W. Pfleiderer and K.-H. Schundehutte, Justus Liebigs Ann. Chem., 612, 158 (1958).
29. S. Senda, K. Hirota, G.-N., Yang, and M. Shirahashi, Yakugaku Zasshi, 91, 1372 (1971).
30. G. Strauss, Justus Liebigs Ann. Chem., 638, 205 (1960).