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Reissert Compound

(Reissert Reaction)

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr527

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Reissert Compound. Comprehensive Organic Name Reactions and Reagents. 527:2335–2340.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

Reissert has introduced the compound 1-benzoyl-2-cyano-1,2-dihydroquinoline from the reaction between quinoline, benzoyl chloride, and aqueous potassium cyanide and is known as the Reissert compound. Subsequently, this reaction has been further extended and various types of heterocycles have been reported to produce compounds with structures similar to Reissert's dihydroquinoline. It has been observed that Reissert compounds can be easily converted into their conjugated bases through deprotonation and can undergo many reactions that normal alkenes undergo. The present study represents few reactions of particular interest and it has been emphasized that among these reactions, the one that decomposes to aldehyde under acidic conditions provides a route to convert acyl chloride into aldehyde. The formation of the Reissert compound has been modified to occur enantioselectively using TMSCN. Reissert compounds have wide application in organic synthesis.

Keywords:

  • quinoline;
  • benzoyl chloride;
  • acyl cyanodihydroquinoline;
  • 1,6-naphthyridines