A three-component Fischer indole synthesis

Nature Protocols
Christopher A Simoneau, Bruce Ganem

Abstract

This protocol describes a three-component approach to multiply-substituted indoles from nitriles, organometallic reagents and arylhydrazine hydrochloride salts. The condensation of organolithium or Grignard reagents with nitriles produces metalloimines, which under acidic conditions and in the presence of arylhydrazines lead to arylhydrazones, the starting materials for the Fischer indole reaction. Combining this approach with the Fischer indole reaction produces indoles in an efficient, one-pot process. The procedure takes approximately 20 h to complete: 3 h for metalloimine formation, 15 h for the Fischer indole reaction and 2 h for isolation and purification.

References

Aug 17, 2002·Organic Letters·Changsheng CaoAaron L Odom
Jul 14, 2006·Chemical Reviews·Guy R Humphrey, Jeffrey T Kuethe

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Citations

Mar 7, 2012·Chemical Reviews·Morteza Shiri
Dec 29, 2020·Organic & Biomolecular Chemistry·Christopher A Hughes-Whiffing, Alexis Perry

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