Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols

Zhou Sun; Kuirong Xiang; Hua Tao; Liqun Guo; Ying Li

doi:10.1039/C8OB01731J

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Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols†

Zhou Sun,^a Kuirong Xiang,^a Hua Tao,^b Liqun Guo^a and Ying Li

*^a

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* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou, P. R. of China
E-mail: liying@lzu.edu.cn
Fax: +86-931-8912582

^b Northwest Institute of Eco-Environmental and Resorce, CAS, China

Abstract

A TMSCl-mediated cascade annulation of isatin-derived propargylic alcohols for the synthesis of 2-substituted 3-chlorobenzofurans is now reported. Mechanistic investigations showed that this proceeded through a sequential Meyer–Schuster rearrangement/nucleophilic addition/intramolecular annulation. TMSCl not only acts as a promoter, but also acts as a chlorine source in this protocol.

This article is part of the themed collection: Synthetic methodology in OBC

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DOI: https://doi.org/10.1039/C8OB01731J
Article type: Paper
Submitted: 19 Jul 2018
Accepted: 06 Aug 2018
First published: 08 Aug 2018

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Org. Biomol. Chem., 2018,16, 6133-6139

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Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols

Z. Sun, K. Xiang, H. Tao, L. Guo and Y. Li, Org. Biomol. Chem., 2018, 16, 6133 DOI: 10.1039/C8OB01731J

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Organic & Biomolecular Chemistry

Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols†

Abstract

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Synthesis of 2-substituted 3-chlorobenzofurans via TMSCl-mediated nucleophilic annulation of isatin-derived propargylic alcohols

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