A GENERAL APPROACH TO 4-UNSUBSTITUTED AND 4-ALKYL-SUBSTITUTED 5-ACYL-1,2,3,4-TETRAHYDROPYRIMIDINE-2-THIONES(ONES) VIA α-(THIO)UREIDOALKYLATION OF 1,3-DIKETONES OR β-OXOESTERS

Abstract

A new general approach to a large variety of hitherto hardly accessible 4-unsubstituted and 4-alkyl-substituted 5-acyl-1,2,3,4-tetrahydropyrimidine-2-thiones(ones) has been developed. The approach is based on the reaction of enolates of various 1,3-diketones or β-oxoesters with readily available N-[alkyl(tosyl)methyl]thioureas, N-(azidomethyl)thiourea, and N-[alkyl(tosyl)methyl]ureas followed by TsOH-catalyzed dehydration of the intermediate 4-hydroxyhexahydropyrimidine-2-thiones(ones) without or with isolation of the latter.