Reactions of 5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazole-2-thione with electrophiles

被引：11
|
作者：
Smicius, R [1 ]
Jakubkiene, V [1 ]
Burbuliene, MM [1 ]
Vainilavicius, P [1 ]
机构：
[1] Vilnius State Univ, Fac Chem, Dept Organ Chem, LT-2006 Vilnius, Lithuania
来源：
MONATSHEFTE FUR CHEMIE | 2002年 / 133卷 / 02期
关键词：
5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazole-2-thione; alkylation; aminomethylation; bromination; nitration;
D O I：
10.1007/s706-002-8247-7
中图分类号：
O6 [化学];
学科分类号：
0703 ;
摘要：
Treatment of 5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazole-2-thione with haloalkanes yielded oxadiazole S-alkyl derivatives, whereas its reaction with formaldehyde and amines resulted in formation of oxadiazole N(3)-aminomethyl derivatives. The alkylation of 2-alkylsulfanyl-5-(6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazoles with methyl bromoacetate proceeded at the N(1)-position of pyrimidine to give 2-alkylsulfanyl-5-(1-methoxycarbonylmethyl-6-methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazoles, whereas aminomethylation, bromination, or nitration took place at position 5 of pyrimidine ring and afforded the corresponding 5-pyrimidine substituted derivatives.
引用
收藏
页码：173 / 181
页数：9
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