ChemInform Abstract: Efficient and Benign One‐Pot Conversion of N‐Tosyl‐1,4,5,6‐tetrahydropyrimidines to Pyrimidines via Tandem β‐Elimination and Aromatization.

Abstract

Abstract An efficient, mild, benign, and practical method for one-pot conversion of N-tosyl-1,4,5,6-tetrahydropyrimidines into pyrimidines is discussed in detail. In this method, N-tosyl-1,4,5,6-tetrahydropyrimidines are first prepared via N-tosylation of tetrahydropyrimidines with TsCl and then treated with 1.5 equivalents of NaOH in dimethylsulfoxide (DMSO) under air at 60 °C to afford corresponding pyrimidines in 70–95% yields via cascade β-elimination and aromatization. [Supplementary materials are available for this article. Go to the publisher's online edition of Synthetic Communications® for the following free supplemental resources: Full experimental and spectral details.]