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 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 63 Issue: 30
  • Publication Date: 2007
  • Doi Number: 10.1016/j.tet.2007.04.088
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.7229-7239
  • Kocaeli University Affiliated: Yes

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.