Oxidative cyclization of 3-oxopropanenitriles with alpha,beta-unsaturated amides by manganese(III) acetate. Regio- and stereoselective synthesis of 4-cyano-2,3-dihydrofuran-3-carboxamides


Burgaz E. V. , YILMAZ M. , Pekel A. T. , Oektemer A.

TETRAHEDRON, vol.63, no.30, pp.7229-7239, 2007 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Volume: 63 Issue: 30
  • Publication Date: 2007
  • Doi Number: 10.1016/j.tet.2007.04.088
  • Title of Journal : TETRAHEDRON
  • Page Numbers: pp.7229-7239

Abstract

4-Cyano-2,3-dihydrofuran-3-carboxamides were obtained from the oxidative cyclization of 3-oxopropanenitriles with unsaturated amides using manganese(III) acetate. Treatment of 3-oxopropanenitriles with (2E)-3-(5-methyl-2-furyl)acrylamide and (2E)-3-(2thienyl)acrylamide gave 2-(5-methyl-2-furyl) and 2-(2-thienyl) substituted 4-cyano-2,3-dihydrofuran-3-carboxamides in moderate yields, respectively. However, (2E)-3-(2-furyl)acrylamide and (2E)-3-phenylacrylamide did not produce any product under the same conditions. On the other hand, reaction of a dienamide such as (2E,4E)-5-phenylpenta-2,4-dienamide with 3-oxopropanenitriles gave diastereomeric mixtures of 2-(2-vinylphenyl)-4-cyano-2,3-dihydrofuran-3-carboxamides. Mechanisms are proposed for the formation of all of these compounds. (C) 2007 Elsevier Ltd. All rights reserved.