An effective new synthesis of 2-aminopyrrole-4-carboxylates

Demir A., Emrullahoglu M.

TETRAHEDRON, vol.61, no.44, pp.10482-10489, 2005 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 61 Issue: 44
  • Publication Date: 2005
  • Doi Number: 10.1016/j.tet.2005.08.050
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.10482-10489
  • Middle East Technical University Affiliated: Yes

Abstract

Efficient syntheses of 2-aminopyrroles are presented starting from beta-dicarbonyl compounds, bromoacetonitrile, and amines. Alkylation of beta-dicarbonyl compounds with bromoacetonitrile furnished alpha-cyanomethyl-beta-dicarbonyl compounds. The condensation reaction of alpha-cyanomethyl-beta-dicarbonyl compounds with amines catalyzed by p-TsOH affords the corresponding enamines in good yields. Base catalyzed cyclization via the addition of an amine moiety to the carbon-nitrogen triple bond of nitrile furnished 2-aminopyrroles in high yields. (c) 2005 Elsevier Ltd. All rights reserved.