Journal
ORGANIC & BIOMOLECULAR CHEMISTRY
Volume 18, Issue 14, Pages 2661-2671Publisher
ROYAL SOC CHEMISTRY
DOI: 10.1039/d0ob00317d
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Funding
- National Natural Science Foundation of China [21572017, 21772010]
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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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