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Metal-free and regiospecific synthesis of 3-arylindoles

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Abstract

A convenient, metal-free, and organic acid–base promoted synthetic method to prepare 3-arylindoles from 3-aryloxirane-2-carbonitriles and arylhydrazine hydrochlorides has been developed. In the reaction, the organic acid catalyzes a tandem nucleophilic ring-opening reaction of aryloxiranecarbonitriles and arylhydrazine hydrochlorides and Fischer indolization. The organic base triethylamine plays a crucial role in the final elimination step in the Fischer indole synthesis, affording 3-arylindoles regiospecifically. The reaction features advantages of microwave acceleration, non-metal participation, short reaction time, organic acid–base co-catalysis, and broad substrate scope.

Graphical abstract: Metal-free and regiospecific synthesis of 3-arylindoles

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Article information


Submitted
13 Feb 2020
Accepted
10 Mar 2020
First published
11 Mar 2020

Org. Biomol. Chem., 2020, Advance Article
Article type
Paper

Metal-free and regiospecific synthesis of 3-arylindoles

C. Xu, W. Xie and J. Xu, Org. Biomol. Chem., 2020, Advance Article , DOI: 10.1039/D0OB00317D

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