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Castro Indole Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr135

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Castro Indole Synthesis. Comprehensive Organic Name Reactions and Reagents. 135:616–618.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The synthesis of indoles by cuprous halide catalyzed intramolecular cyclization of o-ethynylanilines or the coupling between o-haloaniline and cuprous mono-substituted acetylide is generally referred to as the Castro indole synthesis. This reaction is found to be suitable for the preparation of 2-substituted indoles and can be applied as an alternative for Fischer indole synthesis. The reactivity of o-haloanilines, catalytic efficiency of cuprous salts and solvent effect has been analyzed for this reaction and it has been reported that indoles can be synthesized in two steps: Castro–Stephens coupling in pyridine and Castro indole synthesis in DMF.

Keywords:

  • o-ethynylanilines;
  • o-haloanilines;
  • indoles;
  • N-benzylindole