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.]
GRAPHICAL ABSTRACT
![](/cms/asset/725faa84-43c0-4dc3-a8af-dfcc5d697e60/lsyc_a_764433_o_uf0001.gif)
ACKNOWLEDGMENTS
We thank the National Natural Science Foundation of China (No. 20972048) and the Shanghai Educational Development Foundation (Dawn Program No. 03SG27) for the financial support of this work.
Notes
a Isolated yield.
b Reflux.
a Isolated yield.