Two-step route to indoles and analogues from haloarenes: a variation on the Fischer indole synthesis

J Org Chem. 2012 Feb 3;77(3):1217-32. doi: 10.1021/jo201866c. Epub 2011 Oct 14.

Abstract

In a new variation on the Fischer indole synthesis, readily available haloarenes are converted into a wide range of indoles in just two steps by halogen-magnesium exchange and quenching with di-tert-butyl azodicarboxylate, followed by reaction with aldehydes or ketones under acidic conditions. The protocol, which is readily extended to the preparation of indole isosteres, 4- and 6-azaindoles and thienopyrroles, obviates the need to prepare potentially toxic aryl hydrazines, simultaneously avoiding undesirable anilines such as naphthylamines.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Chemistry Techniques, Synthetic / methods*
  • Green Chemistry Technology
  • Halogenation*
  • Hydrocarbons, Aromatic / chemistry*
  • Indoles / chemical synthesis*
  • Indoles / chemistry*
  • Magnesium / chemistry

Substances

  • Hydrocarbons, Aromatic
  • Indoles
  • Magnesium