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Erlenmeyer-Plöchl Azlactone Synthesis

Published Online: 15 SEP 2010

DOI: 10.1002/9780470638859.conrr217

Comprehensive Organic Name Reactions and Reagents

Comprehensive Organic Name Reactions and Reagents

How to Cite

2010. Erlenmeyer-Plöchl Azlactone Synthesis. Comprehensive Organic Name Reactions and Reagents. 217:997–1000.

Publication History

  1. Published Online: 15 SEP 2010

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Abstract

The Erlenmeyer–Plöchl azlactone synthesis is the preparation of azlactones (also called oxazolones) in a Z configuration (originally assigned to the E configuration) by condensation of aromatic aldehydes with hippuric acid (the benzoyl glycine derivatives) in the presence of acetic anhydride. The azlactones are useful for the synthesis of α-ketos, a-amino acids and peptides. The transacylation often occurs in this reaction, especially when the reaction mixture is refluxed.

Keywords:

  • azlactone;
  • hippuric acid;
  • polyphosphoric acid (PPA);
  • acetic anhydride