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Sandmeyer Isatin Synthesis

(Sandmeyer Synthesis)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr557

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Sandmeyer Isatin Synthesis. Comprehensive Organic Name Reactions and Reagents. 557:2467–2470.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The synthesis of isatin derivative involving the condensation of chloral (i.e., trichloroacetaldehyde), hydroxylamine, and a primary aryl amine to an α-isonitrosoacetanilide and subsequent electrophilic cyclization of the latter in the presence of a strong acid such as concentrated sulfuric acid is generally known as the Sandmeyer isatin synthesis. There are several usages of isatin derivatives in organic preparation. The study finds that oximino intermediate from the meta-substituted aryl amine may form two stereoisomers. However, in some of the cases this reaction fails to convert the oximino intermediates into their corresponding isatin derivatives.

Keywords:

  • α-isonitrosoacetanilide;
  • isatin;
  • oximino intermediate;
  • quinolines