Synthetic Communications

Efficient and Benign One-Pot Conversion of N-Tosyl-1, 4, 5, 6-tetrahydropyrimidines to Pyrimidines via Tandem β-Elimination and Aromatization

…, J Dong, XX Shi, X Lu, Q Zhang

Index: Trieu, Tien Ha; Dong, Jing; Shi, Xiao-Xin; Lu, Xia; Zhang, Qiang Synthetic Communications, 2013 , vol. 43, # 23 p. 3141 - 3152

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Citation Number: 2

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.