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Nenitzescu Indole Synthesis

(Nenitzescu Reaction, Nenitzescu Synthesis)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr459

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Nenitzescu Indole Synthesis. Comprehensive Organic Name Reactions and Reagents. 459:2042–2045.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The synthesis of a 5-hydroxyindole derivative involving the condensation between a 1,4-benzoquinone and a β-amino-α,β-unsaturated compound and subsequent cyclization is generally known as the Nenitzescu indole synthesis. It has been observed that the synthesized indole derivatives by this reaction are restricted to those with an electron withdrawing group at position 3. In addition, the completion of this reaction requires an appropriate oxidizing agent to convert the initial adduct into the indole derivative. From monosubstituted quinone, 4-, 6- and 7-substituted 5-hydroxyindole derivatives all are possible products, but 6-substituted isomer is the one normally obtained. This reaction has been modified by using quinone mono-ketals to control the regioselectivity. This reaction is particularly useful for the preparation of 5-hydroxyindole derivatives.

Keywords:

  • 1,4-benzoquinone;
  • 5-hydroxyindole derivative;
  • 2-methyl 1,4-benzoquinone;
  • indole derivative