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Madelung Indole Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr402

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Madelung Indole Synthesis. Comprehensive Organic Name Reactions and Reagents. 402:1791–1794.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The synthesis of indole derivatives by means of the treatment of ortho-alkyl N-acylaniline with a strong base (e.g., potassium alkoxide) at high temperature (e.g., 300–400°C), is generally referred to as the Madelung indole synthesis. This reaction has been modified by using lithium amide or butyl lithium as base so that the reaction can take place at milder conditions. This reaction is useful for the preparation of unsubstituted indole and indoles with substitutents at 2-position.

Keywords:

  • ortho-alkyl N-acylaniline;
  • sodium amide;
  • lithium amide;
  • ortho-alkyl N-benzoyl anilines