Diversity of rearrangement of 3-substituted 5-carbamoyl-1-phenyluracil derivatives

Heterocycles

Volumn 50, Issue 1, 1999, Pages 385-392

  Sajiki, Hironao ^a   Fujita, Yoshiaki ^a   Niimoto, Itaru ^a   Hirota, Kosaku ^a  

^a GIFU PHARMACEUTICAL UNIVERSITY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

5 CARBAMOYL 1 PHENYLURACIL; UNCLASSIFIED DRUG; URACIL DERIVATIVE;

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL BINDING; CHEMICAL BOND; CHEMICAL REACTION; REACTION ANALYSIS;

EID: 0032838262     PISSN: 03855414     EISSN: None     Source Type: Journal    
DOI: 10.3987/com-98-s(h)67     Document Type: Article

References (14)

1. For review see: H. C. van der Plas, Ring Transformations of Heterocycles; Vol. 1 and 2, Academic Press, London, 1973.
2. For review see: H. Wamhoff, J. Dzenis, and K. Hirota, Advances in Heterocyclic Chemistry; ed. by A. R. Katritzky, Vol. 55, Academic Press, New York, 1992, pp. 129-259.
3. (a) K. Hirota, Y. Kitade, H. Sajiki, and Y. Maki, Tetrahedron Lett., 1986, 27, 3263.
4. (b) K. Hirota, Y. Kitade, H. Sajiki, Y. Maki, and M. Yogo, J. Chem. Soc., Perkin Trans, 1, 1990, 367.
5. (a) K. Hirota, H. Sajiki, Y. Kitade, and Y. Maki, J. Chem. Soc., Perkin Trans, 1, 1989, 1695.
6. (b) K. Hirota, H. Sajiki, P-Z. Ni, Y. Kitade, and Y. Maki, Tetrahedron, 1990, 46, 3431.
7. L. Capuano, M. Kussler, and H. R. Kirn, Ann. Uni. Sarav., Math.-Naturwiss. Fak., 1981, 16, 7 (Chem. Abstr., 1982, 96, 85503w).
8. L. Capuano, M. Kussler, and H. R. Kirn, Ann. Uni. Sarav., Math.-Naturwiss. Fak., 1981, 16, 7 (Chem. Abstr., 1982, 96, 85503w).
9. The reaction using 1 molar equivalent of NaH did not go to completion. Therefore, we applied 3 equivalents of NaH for the rearrangement taking into account the convenience for a progress of the reaction.
10. For convenient drawings, the rearrangement products are represented as the barbituric acid forms (5 and 7). Unchanged starting materials (5a) and (5b) were not detected in the reaction mixture.
11. S. Senda, K. Hirota, and J. Notani, Chem. Pharm. Bull., 1972, 20, 1389.
12. S. Senda, K. Hirota, and T. Asao, Chem. Pharm. Bull., 1974, 22, 189.
13. S. Senda, K. Hirota, and J. Notani, Chem. Pharm. Bull., 1972, 20, 1380.
14. T. Shioiri, K. Ninomiya, and S. Yamada, J. Am. Chem. Soc., 1972, 94, 6203.