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Synthesis 2009(10): 1615-1622  
DOI: 10.1055/s-0028-1088051
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Regioselective Synthesis of 5H-Thiazolo[3,2-a]pyrimidin-5-ones from Morita-Baylis-Hillman Adduct Acetates under Solvent-Free and Base-Free Conditions

Weihui Zhong, Baoming Guo, Fuliang Lin, Yongliang Liu, Weike Su*
Key Laboratory of Pharmaceutical Engineering of Ministry of Education, College of Pharmaceutical Sciences, Zhejiang University of Technology, Hangzhou 310014, P. R. of China
Fax: +86(571)88320752; e-Mail: suweike@zjut.edu.cn;
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Publication History

Received 2 December 2008
Publication Date:
20 April 2009 (online)

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Abstract

5H-Thiazolo[3,2-a]pyrimidin-5-ones were easily prepared in good to excellent yields with high regioselectivity by nucleophilic addition of thiazol-2-amines to Morita-Baylis-Hillman adduct acetates, followed by cyclization and a thermo-sigmatropic shift procedure under solvent-free and base-free conditions.

Key words

fused-ring systems - heterocycles - α,β-unsaturated esters - thiazol-2-amines - solvent-free - base-free