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Saegusa Cyclization

(Saegusa Indole Synthesis)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr555

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Saegusa Cyclization. Comprehensive Organic Name Reactions and Reagents. 555:2458–2461.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The synthesis of indole and 2- or 3-substituted indole derivatives by means of the lithiation of ortho-alkyl phenyl isocyanide and subsequently intramolecular cyclization is generally known as the Saegusa cyclization. This reaction is solvent dependent and can give indoles in quantitative yields. The synthesis of indole derivatives has been discussed for o-tolyl isocyanide and o-lithomethylphenyl isocyanide. This reaction has certain application in the preparation of indole derivatives.

Keywords:

  • ortho-alkyl phenyl isocyanide;
  • o-tolyl isocyanide;
  • N,N-diisopropyl-N′-(o-tolyl)-formamidine;
  • 3-acyl indoles