Molecular Diversity 2011-02-01

Convenient synthesis of polyfunctional dihydrothiophenes with tandem reaction of 1,3-thiazolidinedione, aldehyde, arylamine and ethyl cyanoacetate.

Jing Sun, Er-Yan Xia, Rong Yao, Chao-Guo Yan

Index: Mol. Divers. 15(1) , 115-23, (2011)

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Abstract

New, highly-functionalized dihydrothiophenes are conveniently synthesized from the novel tandem, four-component reactions of 1,3-thiazolidinedione, aldehyde, arylamine, and ethyl cyanoacetate, catalyzed by triethylamine. The reaction mechanism involves the use of Knoevenagel condensation, Michael addition, and ring-opening of 1,3-thiazolidinedione, followed by intramolecular ring closure process. The reaction is diastereoselective and only trans-2,3-dihydrothiophenes were produced in moderate yields. The functionalized dihydrothiophenes can be converted efficiently to the corresponding thiophenes by DCC dehydrogenation reaction.