Synthesis of radialene-shaped pyrroles by multiple-anion-capture reactions of 1,3-dianions

Chemistry. 2001 Jun 18;7(12):2617-27. doi: 10.1002/1521-3765(20010618)7:12<2617::aid-chem26170>3.0.co;2-f.

Abstract

A new multicomponent reaction (multiple-anion-capture reaction) of 1,3-dianions with nitriles and oxalic acid-bis(imidoyl)chlorides is reported. This process allows for an efficient and regioselective synthesis of a variety of radialene-shaped pyrroles which constitute structurally new and interesting heterocyclic systems. The cyclization products can be considered as aza-analogues of the pharmacologically relevant substance class of 3-acetyltetramic acids. A rationalization of the experimental results is given based on quantum chemical computations.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Anions
  • Crystallography, X-Ray
  • Cyclization
  • Models, Molecular
  • Nitriles
  • Oxalates
  • Pyrroles / chemical synthesis*

Substances

  • Anions
  • Nitriles
  • Oxalates
  • Pyrroles