Zinc perchlorate catalyzed one-pot amination-annulation of alpha-cyanomethyl-beta-ketoesters in water. Regioselective synthesis of 2-aminopyrrole-4-carboxylates

Demir A., Emrullahoglu M.

TETRAHEDRON, vol.62, no.7, pp.1452-1458, 2006 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 62 Issue: 7
  • Publication Date: 2006
  • Doi Number: 10.1016/j.tet.2005.11.018
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.1452-1458
  • Keywords: aminopyrroles, amination, hetero annulation, GABA analogs, 1.3-dicarbonyls, 2-SUBSTITUTED PYRROLE DERIVATIVES, AMINO-ALCOHOLS, CONJUGATED AZOALKENES, ANTIVIRAL ACTIVITY, HOMOCHIRAL AMINES, ENAMINO ESTERS, CONVERSION, ANALOGS, 1-AMINOPYRROLES, ALKYNES
  • Middle East Technical University Affiliated: Yes

Abstract

In this paper, we report the efficient and regioselective synthesis of 2-aminopyrrole-4-carboxylates as derivatives of conformationally restricted analogues of gamma-amino butyrates (GABA) via a zinc perchlorate catalyzed amination-annulation of alpha-cyanomethyl-beta-ketoesters under mild reaction conditions in water. (c) 2005 Elsevier Ltd. All rights reserved.