Metal-free and regiospecific synthesis of 3-arylindoles?
Organic & Biomolecular Chemistry Pub Date: 2020-03-11 DOI: 10.1039/D0OB00317D
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.
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Journal Name：Organic & Biomolecular Chemistry
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CAS no.: 89640-58-4
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