Synthesis of 2,3-dihydro-1 3-thiazin-4(1H)ones and their remarkably facile recyclization to 2,3-dihydropyrimidin-4(1H)-ones

被引：14

作者：

Vovk, MV ^{[1
]}

Sukach, VA ^{[1
]}

Chernega, AN ^{[1
]}

Pyrozhenko, VV ^{[1
]}

Bol'but, AV ^{[1
]}

Pinchuk, AM ^{[1
]}

机构：

[1] Natl Acad Sci Ukraine, Inst Organ Chem, Kiev, Ukraine

来源：

HETEROATOM CHEMISTRY | 2005年 / 16卷 / 05期

关键词：

D O I：

10.1002/hc.20129

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Functionalized2,3-dihydro-1,3-thiazin-4 (1 H)-one derivatives have been synthesized by cyclo-condensation of 3-alkyl(aryl)amino-2-cyano-3-mercaptoacrylamides with aldehydes and ketones under acidic catalysis. 6-Alkyl(aryl)amino-5-cyano-2,3-dihydro- 1, 3-thiazin-4 (1H)-ones, when treated with a dilute solution of potassium hydroxide, are converted into the potassium salts of isomeric compounds, 1-alkyl(aryl)-5-cyano-6-mercapto-2,3-dihydropyrimidin-4(1H)-ones. Alkylation of the latter with dimethyl sulfate in situ furnishes 1-alkyl(aryl)-6-alkylthio-5cyano-2,3-dihydropyrimidin-4(1H)-ones, whereas boiling them in ethanol with an excess of hydrochloric acid leads to starting 2,3-dihydro-1,3-thiazin-4(1H)ones. (c) 2005 Wiley Periodicals, Inc.

引用

页码：426 / 436

页数：11

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