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, cilt.73, ss.4335-4340, 2017 (SCI İndekslerine Giren Dergi) identifier identifier

  • Cilt numarası: 73 Konu: 30
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.tet.2017.05.092
  • Dergi Adı: TETRAHEDRON
  • Sayfa Sayıları: ss.4335-4340


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.