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■ Synthesis of Novel Benzofuro-Fused Thiazolo[3,2-a]pyrimidinones via Pictet-Spengler Reaction

Dao-Lin Wang,* Dong Wang, Jian-Hua Qiang, and Lin Liu

*Liaoning Key Laboratory of Synthesis and Application of Functional Compound, College of Chemistry & Chemical Engineering, Bohai University, Jinzhou 121001, China

Abstract

An efficient method for the preparation of novel benzofuro[3’,2’:2,3]pyrido[4,5:d]thiazolo[3,2-a]pyrimidin-5-ones 5 is described. The key intermediate, 7-(3-amino-2-benzofuran)-5H-thiazolo[3,2-a]pyrimidin-5-one (3), was synthesized from 7-(chloromethyl)-5H-thiazolo[3,2-a]pyrimidin-5-one (1) with salicylonitrile (2) by Thorpe-Ziegler isomerization. Subsequent reaction of the intermediate amine with aromatic aldehydes via Pictet-Spengler reaction provided benzofuro-fused thiazolo[3,2-a]pyrimidines under sulfamic acid as catalyst in good yields.