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 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 63 Issue: 2
  • Publication Date: 2007
  • Doi Number: 10.1016/j.tet.2006.10.054
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.461-468

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.