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

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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.

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Correspondence to Chao-Guo Yan.

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Sun, J., Xia, EY., Yao, R. et al. Convenient synthesis of polyfunctional dihydrothiophenes with tandem reaction of 1,3-thiazolidinedione, aldehyde, arylamine and ethyl cyanoacetate. Mol Divers 15, 115–123 (2011). https://doi.org/10.1007/s11030-010-9278-x

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  • DOI: https://doi.org/10.1007/s11030-010-9278-x

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