Reaction of ethyl 4-aryl-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates with N-methylmorpholinium 3-cyano-1,4-dihydro- and 3-cyano-1,4,5,6-tetrahydropyridine-2-thiolates

被引：0

作者：

V. V. Dotsenko

I. A. Lebedeva

S. G. Krivokolysko

M. V. Povstyanoi

V. M. Povstyanoi

E. O. Kostyrko

机构：

[1] ʻʻChemExʼʼ Laboratory,

[2] Vladimir Dalʼ East Ukrainian National University,undefined

[3] Kherson National Technical University,undefined

[4] A. A. Bogomolets National Medical University,undefined

来源：

Chemistry of Heterocyclic Compounds | 2012年 / 48卷

关键词：

Biginelli dihydropyrimidines; -methylmorpholinium 1,4-dihydropyridine-2-thiolates; -methylmorpholinium 1,4,5,6-tetrahydropyridine-2-thiolates; alkylation; biological activity; oxidation; Thorpe-Ziegler reaction;

D O I：

暂无

中图分类号：

学科分类号：

摘要：

Alkylation of N-methylmorpholinium 4-Ar1-3-cyano-6-oxo-1,4,5,6-tetrahydropyridine-2-thiolates using ethyl 4-Ar-6-bromomethyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (10 % KOH, DMF) gives mixtures of diastereomers of ethyl 4-Ar-6-[(4-Ar1-3-cyano-1,4,5,6-tetrahydropyridin-2-ylthio)methyl]-1-methyl-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates in overall 30-58 % yield. Under these conditions the N-methylmorpholinium 4-Ar1-5-(N-Ar2-carbamoyl)-3-cyano-6-methyl-1,4-dihydropyridine-2-thiolates undergo aromatization of the dihydropyridine ring to give ethyl 4-Ar-6-[4-Ar1-5-(N-Ar2-carbamoyl)-3-cyano-6-methylpyridin-2-ylthio)methyl]-2-oxo-1,2,3,4-tetrahydropyrimidine-5-carboxylates (37-51 %). In the absence of KOH, only the substituted pyridine-2(1 H)-thione is formed as a product of oxidation of the dihydropyridine ring in the starting substrate. Some of the alkylation products obtained possess weak or moderate antibacterial activity towards the specific strains of Escherichia coli and Bacillus subtilis but are inactive towards Candida albicans and Staphylococcus aureus.

引用

页码：462 / 469

页数：7

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