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Short Paper | Regular issue | Vol 92, No. 12, 2016, pp.2244-2251
Published online, 10th November, 2016
DOI: 10.3987/COM-16-13573
Methodology to Access Thiazo[3’,2’:2,3]pyrido[4,5-d]thiazolo[3,2-a]pyrimidinones

Dao-Lin Wang,* Dong Wang, Qiao-Min Li, and Jian-Hua Qian

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

Abstract

A synthesis of model thiazolo[3’,2’:2,3]pyrido[4,5-d]thiazolo[3,2-a] pyrimidin-5-ones (5), based on the classical Pictet-Spengler method, is described. The key intermediate, 7-(3-amino-5-phenylaminothiazol-2-yl)-5H-thiazolo [3,2-a]pyrimidin-5-one (3), was synthesized from 7-chloromethyl-5H-thiazolo [3,2-a]pyrimidin-5-one (1) with potassium N-phenyl-N'-cyanoimidothiocarbonate (2) by Thorpe-Ziegler isomerization. Cyclocondensation of the intermediate amine with aromatic aldehydes, using sulfamic acid under Pictet-Spengler reaction conditions, delivered the target compounds 5a-m