A novel ring transformation of 5-acylaminouracils and 5-acylamino-pyrimidin-4(3H)-ones into imidazoles

作者: Taisei Ueda , Izumi Matsuura , Nobutoshi Murakami , Shin-ichi Nagai , Jinsaku Sakakibara

DOI: 10.1016/S0040-4039(00)80560-2

关键词:

摘要: Abstract 1, 3-Disubstituted 5-acylamino-6-methyluracils (2a-e) were transformed into 2-disubstituted 4-alkylcarbamoyl-5-methyl-1 H -imidazoles (3a-e) by treatment with 5% aqueous sodium hydroxide in ethanol. Similarly, reaction of 5-acylamino-6-methyl-3-phenyl-4-(3 )-pyrimidinones (5a-d) ethanol gave 2-substituted 5-methyl-4-phenylcarbamoyl-1 (6a-d).

参考文章(10)
CHOJI KASHIMA, AKIRA KATOH, YUKO YOKOTA, YOSHIMORI OMOTE, Ring Transformation Reaction of 1, 4, 6-Trisubstituted 2 (1H)-Pyrimidinones and -Thiones with Hydroxylamine Chemical & Pharmaceutical Bulletin. ,vol. 29, pp. 2516- 2519 ,(1981) , 10.1248/CPB.29.2516
Taisei Ueda, Jinsaku Sakakibara, NOVEL RING TRANSFORMATION OF 5-AMINO-4 (3H)-PYRIMIDINONES INTO IMIDAZOLES AND IMIDAZOLES INTO A 1, 2, 4-TRIAZINE Chemical & Pharmaceutical Bulletin. ,vol. 32, pp. 2863- 2865 ,(1984) , 10.1248/CPB.32.2863
AKIRA KATOH, YOSHIMORI OMOTE, CHOJI KASHIMA, Ring Transformation Reactions of 1-Substituted 2 (1H)-Pyrimidinones and Related Compounds with Active Methylene Compounds Chemical & Pharmaceutical Bulletin. ,vol. 32, pp. 2942- 2946 ,(1984) , 10.1248/CPB.32.2942
RG Dickinson, NW Jacobsen, RG Gillis, The hydrazinolysis of heterocyclic compounds. I. 1,4,6-Trimethylpyrimidine-2(1H)-thione and related compounds Australian Journal of Chemistry. ,vol. 28, pp. 859- 870 ,(1975) , 10.1071/CH9750859
Shigeo Senda, Kosaku Hirota, Kazuo Banno, Ring contraction of uracils to hydantoins Tetrahedron Letters. ,vol. 15, pp. 3087- 3088 ,(1974) , 10.1016/S0040-4039(01)91830-1
Brian A. Otter, Isaac M. Sasson, R. Paul Gagnier, New hydantoin synthesis via a reactive 5-oxo-6-methylenepyrimidine intermediate Journal of Organic Chemistry. ,vol. 13, pp. 508- 513 ,(1982) , 10.1021/JO00342A027
Jack J. Fox, Tsann Long Su, Lloyd M. Stempel, Kyoichi Watanabe, PYRIMIDINES. 18. A NOVEL PYRIMIDINE TO BENZENE RING TRANSFORMATION REACTION. . CONVERSION OF 5-NITRO-2(1H)-PYRIMIDINONE INTO P-NITROPHENOL DERIVATIVES Journal of Organic Chemistry. ,vol. 13, pp. 1081- 1084 ,(1982) , 10.1021/JO00345A037