Synthesis 2016; 48(23): 4131-4142
DOI: 10.1055/s-0035-1562613
paper
© Georg Thieme Verlag Stuttgart · New York

Intramolecular Mizoroki–Heck Reaction of 2-Thiosubstituted Acrylates for the Synthesis of 3-Substituted Benzo[b]thiophene-2-carboxylates

Se Hun Kwak
Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University, 26, 3-ga, Pil-dong Jung-gu, Seoul 100-715, Korea   Email: ydgong@dongguk.edu
,
Su-Jeong Lim
Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University, 26, 3-ga, Pil-dong Jung-gu, Seoul 100-715, Korea   Email: ydgong@dongguk.edu
,
Hyun-Jeong Yoo
Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University, 26, 3-ga, Pil-dong Jung-gu, Seoul 100-715, Korea   Email: ydgong@dongguk.edu
,
Ji-Eun Ha
Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University, 26, 3-ga, Pil-dong Jung-gu, Seoul 100-715, Korea   Email: ydgong@dongguk.edu
,
Young-Dae Gong*
Center for Innovative Drug Library Research, Department of Chemistry, College of Science, Dongguk University, 26, 3-ga, Pil-dong Jung-gu, Seoul 100-715, Korea   Email: ydgong@dongguk.edu
› Author Affiliations
Further Information

Publication History

Received: 16 June 2016

Accepted after revision: 11 July 2016

Publication Date:
23 August 2016 (online)


Abstract

3-Substituted 2-(phenylthio)acrylates prepared from aldol condensation using titanium tetrachloride were employed to synthesize benzo[b]thiophenes. The acrylates containing aryls and alkyls generated the desired benzo[b]thiophenes in reasonable yields under the optimized Heck condition, but acrylates having heteroaryls gave the desired products in poor yields or no products under the condition.

Supporting Information