4.4 Article

A mild and efficient AgSbF6-catalyzed synthesis of fully substituted pyrroles through a sequential propargylation/amination/cycloisomerization reaction

Journal

TETRAHEDRON
Volume 70, Issue 34, Pages 5267-5273

Publisher

PERGAMON-ELSEVIER SCIENCE LTD
DOI: 10.1016/j.tet.2014.05.073

Keywords

Propargylation; AgSbF6; Cycloisomerization; Pyrrole; Heterocycles

Funding

  1. College of Pharmacy of University of Arkansas for Medical Sciences
  2. National Institutes of Health (NIH) Clinical and Translational Science Award (CTSA) program [UL1TR000039, KL2TR000063]

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Development of an efficient synthesis of fully substituted pyrroles via a sequential propargylation/amination/cycloisomerization was accomplished using AgSbF6 as a catalyst. The one-pot three-component reaction of propargylic alcohols, 1,3-dicarbonyl compounds, and primary amines proceeds at a mild temperature, which prevents the formation of furan by-product. The reaction was also successfully applied to the more basic aliphatic amines with the addition of 1.1 equiv of acetic acid. (C) 2014 Elsevier Ltd. All rights reserved.

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