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■ One-Pot Two-Step Synthesis of N3-Functionalized 3,4-Dihydropyrimidinones in the Presence of TMSCl

Zheng-Jun Quan,* Rong-Guo Ren, Yu-Xia Da, Zhang Zhang, Xiao-Dong Jia, Cai-Xia Yang, and Xi-Cun Wang*

*Gansu Key Laboratory of Polymer Materials, College of Chemistry and Chemical Engineering, Northwest Normal University, Lanzhou, Gansu 730070, China

Abstract

Novel 3,4-dihydropyrimidinones modified with N3-alkyloxymethyl, aminomethyl, arylsulfonylmethyl, and azidomethyl groups can be regioselectively obtained over their isomeric N1 compounds in good yields by reaction of 3,4-dihydropyrimidinones with paraformaldehyde and alcohol, amine, sodium ben-zenesulfinate, and sodium azide, respectively, by a one-pot two-step strategy in the presence of chlorotrimethylsilane. The advantages of this method are the sim-ple procedure, the high regioselectivity of the products, no requirement for a base catalyst, and the mild reaction conditions.