Synthesis 2013; 45(24): 3392-3398
DOI: 10.1055/s-0033-1339917
paper
© Georg Thieme Verlag Stuttgart · New York

A New [2+2+1] Heterocyclization for the Synthesis of 2,3,5-Trisubstituted Thiophenes under Microwave Irradiation

Hai-Wei Xu
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, P. R. of China   Fax: +86(516)83500065   Email: jiangchem@jsnu.edu.cn   Email: laotu@jsnu.edu.cn
,
Guan-Hua Ma
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, P. R. of China   Fax: +86(516)83500065   Email: jiangchem@jsnu.edu.cn   Email: laotu@jsnu.edu.cn
,
Bo Jiang*
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, P. R. of China   Fax: +86(516)83500065   Email: jiangchem@jsnu.edu.cn   Email: laotu@jsnu.edu.cn
,
Shu-Jiang Tu*
School of Chemistry and Chemical Engineering, and Jiangsu Key Laboratory of Green Synthetic Chemistry for Functional Materials, Jiangsu Normal University, Xuzhou, 221116, Jiangsu, P. R. of China   Fax: +86(516)83500065   Email: jiangchem@jsnu.edu.cn   Email: laotu@jsnu.edu.cn
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Publication History

Received: 10 August 2013

Accepted after revision: 16 September 2013

Publication Date:
08 October 2013 (online)


Abstract

A new three-component strategy for the efficient synthesis of 2,3,5-trisubstituted thiophene derivatives through a [2+2+1] heterocyclization between 3-(2-aryl-2-oxoethylidene)-2-oxindoles and α-thiocyanato ketones under microwave irradiation is described. The bond-forming efficiency, accessibility, and generality of this synthesis make it highly valuable to assemble thiophene scaffolds.

Supporting Information