Ring annulation versus alkylation of pyrrole with alpha-phosphoryl-alpha,beta-unsaturated ketones

Tasgin D. I., ÜNALEROĞLU C.

TETRAHEDRON, vol.72, no.39, pp.5934-5942, 2016 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 72 Issue: 39
  • Publication Date: 2016
  • Doi Number: 10.1016/j.tet.2016.08.045
  • Journal Name: TETRAHEDRON
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.5934-5942
  • Hacettepe University Affiliated: Yes

Abstract

In this study; novel aryl, heteroaryl, pyrrolyl and phosphoryl groups containing pyrrolizines were synthesized by the ring annulation reaction of aryl or heteroaryl substituted alpha-phosphoryl-alpha,beta-unsaturated ketones with pyrrole under mild reaction conditions. This domino reaction involves scandium triflate catalyzed addition of pyrrole to the double bond of alpha-phosphoryl-alpha,beta-unsaturated ketones, carbonyl group and finally ring annulation sequences. The presented work provided a convenient way for the synthesis of novel bispyrrolic compounds. (C) 2016 Elsevier Ltd. All rights reserved.