Issue 24, 2021

Construction of 6H-benzo[c]thiochromenes via a tandem reaction of arynes with thionoesters

Abstract

A mild and transition-metal free tandem reaction for the construction of 6H-benzo[c]thiochromenes has been developed. Thionoesters react with two molecules of arynes through a Diels–Alder cycloaddition/nucleophilic arylation process to afford 6-alkoxy-6-aryl-6H-benzo[c]thiochromenes in 37–80% yields. In addition, the Diels–Alder cycloaddition/aromatization tandem reaction of thionoesters with one molecule of aryne provides the construction of 6-alkoxyl-6H-benzo[c]thiochromenes in 51–75% yields.

Graphical abstract: Construction of 6H-benzo[c]thiochromenes via a tandem reaction of arynes with thionoesters

Supplementary files

Article information

Article type
Research Article
Submitted
07 Aug 2021
Accepted
31 Oct 2021
First published
10 Nov 2021

Org. Chem. Front., 2021,8, 6979-6984

Construction of 6H-benzo[c]thiochromenes via a tandem reaction of arynes with thionoesters

Y. An, F. Zhang, G. Du, Z. Cai and L. He, Org. Chem. Front., 2021, 8, 6979 DOI: 10.1039/D1QO01177D

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