New approaches to polysubstituted pyrroles and pyrrolinones from alpha-cyanomethyl-beta-ketoesters

Demir A. S., Emrullahoglu M., Ardahan G.

TETRAHEDRON, vol.63, no.2, pp.461-468, 2007 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 63 Issue: 2
  • Publication Date: 2007
  • Doi Number: 10.1016/j.tet.2006.10.054
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.461-468
  • Keywords: pyrroles, heteroannulation, GABA analogs, 1,3-dicarbonyls, pyrrolinones, AMINO-ALCOHOLS, EFFICIENT SYNTHESIS, HOMOCHIRAL AMINES, DERIVATIVES, COMPLEXES, (R)-1-ACETYL-5-ISOPROPOXY-3-PYRROLIN-2-ONE, 2-AMINOPYRROLE-4-CARBOXYLATES, PYRROLIDIN-2-ONES, NUCLEOPHILES, REACTIVITY
  • Middle East Technical University Affiliated: Yes

Abstract

In this present paper, we report the efficient, regioselective one-pot synthesis of 5-alkoxy and 5-alkylsulfanylpyrrole-3-carboxylates in high yields via the zinc perchlorate-catalyzed addition of alcohols and thiols to the nitrile carbon of alpha-cyanornethyl-beta-ketoesters followed by annulation. The addition-annulation process is undertaken in aqueous solution to give 4,5-dihydro-5-oxo-1H-pyrrole-beta-carboxylates (pyrrolinones) in good yields. These 4,5-dihydro-5-oxo-1H-pyrrole-3-carboxylates are also obtained by the hydrolysis of 5-alkoxypyrrole-3-carboxylates. (c) 2006 Elsevier Ltd. All rights reserved.