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Synthesis 2010(23): 3987-3992  
DOI: 10.1055/s-0030-1258272
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

Diastereoselective Synthesis of trans-2,3-Dihydrothiophenes via Multicomponent Reactions of Pivaloylacetonitrile, Aldehyde, Amine, and Thiazolidinedione

Jing Sun, Qun Wu, Er-Yan Xia, Chao-Guo Yan*
College of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002, P. R. of China
Fax: +86(514)87975244; e-Mail: cgyan@yzu.edu.cn;
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Publication History

Received 26 May 2010
Publication Date:
28 September 2010 (online)

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Abstract

Polyfunctionalized trans-2,3-dihydrothiophenes are efficiently synthesized from the four-component reactions of thiazolidine-2,4-dione, aromatic aldehydes, secondary amines, and pival­-oylacetonitrile. The reaction mechanism involves Knoevenagel condensation, Michael addition, and characteristic ring-opening of thiazolidine-2,4-dione followed by an intramolecular ring-closure process

Key words

multicomponent reaction - thiazolidinedione - pivaloyl­acetonitrile - dihydrothiophene

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