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, sa.30, ss.4335-4340, 2017 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 73 Sayı: 30
  • Basım Tarihi: 2017
  • Doi Numarası: 10.1016/j.tet.2017.05.092
  • Dergi Adı: TETRAHEDRON
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.4335-4340
  • İstanbul Teknik Üniversitesi Adresli: Evet

Özet

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.