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Paal-Knorr Pyrrole Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr475

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Paal-Knorr Pyrrole Synthesis. Comprehensive Organic Name Reactions and Reagents. 475:2107–2110.

Publication History

  1. Published Online: 15 SEP 2010

Abstract

The acid-catalyzed formation of pyrrole derivatives from 1,4-dicarbonyl compounds and ammonia or primary amines is generally known as the Paal–Knorr pyrrole synthesis. This reaction provides a general route for pyrrole derivatives from a variety of 1,4-dicarbonyl compounds and primary amines. The mechanistic study exibits that dl-diastereomers of 3,4-dimethyl or 3,4-diethyl-2,5-hexanediones are faster than their corresponding meso-diastereomers to form pyrroles. Several catalysts have been used for this reaction including Lewis acids. This reaction has been improved by using microwave radiation.

Keywords:

  • titanium (IV) tetra-isopropoxide;
  • cyclohexyl amine;
  • microwave radiation;
  • ammonia