Amberlyst-15 catalyzed Michael addition of beta-dicarbonyl compounds to the enones and unexpected ring closure products


Gunduz H., ECE H., Atsay A., Kumbaraci V., Talinli N.

TETRAHEDRON, vol.73, no.30, pp.4335-4340, 2017 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 73 Issue: 30
  • Publication Date: 2017
  • Doi Number: 10.1016/j.tet.2017.05.092
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.4335-4340
  • Istanbul Technical University Affiliated: Yes

Abstract

Conjugate addition reactions of 2,4-pentandione, dibenzoylmethane and ethylacetoacetate to enones have been investigated using Amberlyst-15 or Amberlyst-15-DMAP acetate system as catalysts. When 2,4-pentandione reactions were carried out in the presence of Amberlyst-15, conjugate addition and/or conjugate -addition initiated ring closure products were obtained depending on the reaction conditions. However, unlike 2,4-pentandione, dibenzoylmethane gave only conjugate addition products with Amberlyst-15. When Amberlyst-15-DMAP acetate system was used, always only conjugate addition products were obtained with beta-dicarbonyl compounds independent of the reaction conditions. (C) 2017 Elsevier Ltd. All rights reserved.