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Gassman Oxindole Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr262

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Gassman Oxindole Synthesis. Comprehensive Organic Name Reactions and Reagents. 262:1194–1197.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

This reaction is a multistep process (but a one-pot reaction) for preparing oxindole with an electron-withdrawing group involving sequential treatment of aniline with tert-butyl hypochlorite, ethyl (methylthio)acetate, triethylamine, and hydrochloric acid and final treatment with zinc or Raney nickel for the desulfurization and is referred to as the Gassman oxindole synthesis. Further oxidation of the resulting oxindole by N chlorosuccinamide/HgO or by direct air oxidation has been reported to produce relevant isatin. This reaction has been found to tolerate a variety of functional groups, which differ in electron character; besides this, N alkylanilines are also found suitable for this reaction. This reaction is useful in the synthesis of oxindoles and isatins.

Keywords:

  • tert-butyl hypochlorite;
  • triethylamine;
  • N alkylanilines;
  • oxindole