Novel intramolecular rearrangement of 5-carbamoyluraclls into barbituric acids☆
作者： Kosaku Hirota , Hironao Sajiki , Pei-Zhou Ni , Yukio Kitade , Yoshifumi Maki
DOI: 10.1016/S0040-4020(01)81513-1
关键词: Sigmatropic reaction 、 Stereochemistry 、 Chemistry 、 Lactam 、 Intramolecular reaction 、 Sodium ethoxide 、 Thioamide 、 Intramolecular force 、 Carboxamide
摘要: Abstract Heating of 5-carbamoyl- (1) and 5-thiocarbamoyl-3-methyl-1-phenyluracil (5) derivatives in ethanolic sodium ethoxide causes a novel intramolecular rearrangement to give 5-anilinomethylenebarbituric acids(2) 5-anilinomethylene-4-thiobarbituric and(6), respectively.
elsevier.com
sci-hub.se 参考文章(28)
Kosaku HIROTA, Hironao SAJIKI, Yukio KITADE, Yoshifumi MAKI, Rearrangement of 5-Cyanouracils into 6-aminouracils by reaction with amines and hydroxide ion. Chemical & Pharmaceutical Bulletin. ,vol. 37, pp. 2008- 2011 ,(1989) , 10.1248/CPB.37.2008
KOSAKU HIROTA, YUKIO KITADE, KAORU SHIMADA, SHIGEO SENDA, A ring transformation of uracil into the pyrazole ring system. Reinvestigation of the reaction of 5-formyluracils with hydrazines. Chemical & Pharmaceutical Bulletin. ,vol. 29, pp. 3760- 3762 ,(1981) , 10.1248/CPB.29.3760
MINORU SEKIYA, CHIZUKO YANAIHARA, Formic Acid Reduction. VI. Barbituric Acid Derivatives. Reduction of 5-Arylaminomethylene- and 5-Alkylaminomethylene-substituted Barbituric Acids converting to 5-Methylbarbituric Acids Chemical & Pharmaceutical Bulletin. ,vol. 17, pp. 810- 814 ,(1969) , 10.1248/CPB.17.810
Tsann-Long Su, Kyoichi A. Watanabe, Pyrimidines. 21. Novel reactions of 5-cyano-1,3-dimethyluracil with carbon nucleophiles. A facile preparation of certain pyrido[2,3-d]pyrimidines Journal of Heterocyclic Chemistry. ,vol. 21, pp. 1543- 1547 ,(1984) , 10.1002/JHET.5570210560
Kosaku Hirota, Kyoichi A. Watanabe, Jack J. Fox, PYRIMIDINES. 14. NOVEL PYRIMIDINE TO PYRIMIDINE TRANSFORMATION REACTIONS AND THEIR APPLICATION TO C-NUCLEOSIDE CONVERSIONS. A FACILE SYNTHESIS OF PSEUDOISOCYTIDINE Journal of Organic Chemistry. ,vol. 43, pp. 1193- 1197 ,(1978) , 10.1021/JO00400A037
Tsann-Long Su, Kyoichi A. Watanabe, Pyrimidines. 20. Novel reactions of 5‐cyano‐1,3‐dimethyluracil. A simple synthesis of pyrido[2,3‐d]pyrimidines Journal of Heterocyclic Chemistry. ,vol. 19, pp. 1261- 1262 ,(1982) , 10.1002/JHET.5570190563
Kosaku Hirota, Yukio Kitade, Shigeo Senda, A novel ring transformation of uracil into the benzene ring system Journal of Heterocyclic Chemistry. ,vol. 17, pp. 413- 414 ,(1980) , 10.1002/JHET.5570170245
Kwang-Yuen Zee-Cheng, Chai-Chung Cheng, Reactions of hydrazine and methylhydrazine with uracil-5-carboxaldehyde. Unusual pyrimidine-to-pyrazole conversion Journal of Organic Chemistry. ,vol. 33, pp. 892- 894 ,(1968) , 10.1021/JO01266A106
Eileen B. Walsh, Zhu Nai-Jue, Guo Fang, Heinrich Wamhoff, 6-[(Dimethylamino)methylene]amino-1,3-dimethyluracil: A versatile aza-diene substrate for cycloaddition and michael-type reactions Tetrahedron Letters. ,vol. 29, pp. 4401- 4404 ,(1988) , 10.1016/S0040-4039(00)80505-5
Kosaku Hirota, Yoshio Abe, Tetsuji Asao, Shigeo Senda, Yukio Kitade, Yoshifumi Maki, Ring transformation of pyrimidines to pyridines. Synthesis of 4-alkylaminopyridin-2-ones by alkaline hydrolysis of 6-(2-dimethylaminovinyl)uracils Journal of Heterocyclic Chemistry. ,vol. 25, pp. 985- 990 ,(1988) , 10.1002/JHET.5570250354