Reactions of 5-(6-Methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazole-2-thione with Electrophiles |
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Authors: | Romualdas Smicius Virginija Jakubkiene Milda M Burbuliene Povilas Vainilavicius |
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Institution: | (1) Department of Organic Chemistry, Faculty of Chemistry, Vilnius University, LT-2006 Vilnius, Lithuania, LT |
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Abstract: | Summary. 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.
Received May 9, 2001. Accepted (revised) August 17, 2001 |
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Keywords: | , ,5-(6-Methyl-2,4-dioxo-1,2,3,4-tetrahydro-3-pyrimidinyl)-methyl-1,3,4-oxadiazole-2-thione, Alkylation, Aminomethylation, Bromination, Nitration, |
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