TFA catalyzed sequential amination/annulation/aromatization reaction of 2-propynyl-1.3-dicarbonyl compounds with amines: a new one-pot approach to functionalized pyrroles

Demir A., Aybey A., Kayalar M.

ARKIVOC, pp.105-116, 2005 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2005
  • Journal Name: ARKIVOC
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.105-116
  • Middle East Technical University Affiliated: Yes

Abstract

Highly flexible and efficient syntheses of 1,2,3,5- substituted pyrroles starting from 2- propynyl-1,3- dicarbonyl compounds and amines are presented. TFA catalyzed formation of the pyrroles is suggested to proceed through sequential amination of the carbonyl compounds followed by regioselective 5- exo- dig cyclization of the enaminone intermediate and aromatization.