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Direct synthesis of pyrroles from imines, alkynes, and acid chlorides: an isocyanide-mediated reaction.

Authors
  • Cyr, Daniel J St
  • Martin, Nicolas
  • Arndtsen, Bruce A
Type
Published Article
Journal
Organic Letters
Publisher
American Chemical Society
Publication Date
Feb 01, 2007
Volume
9
Issue
3
Pages
449–452
Identifiers
PMID: 17249784
Source
Medline
License
Unknown

Abstract

[reaction: see text] A direct synthesis of pyrroles from imines, acid chlorides, and alkynes mediated by isocyanides is reported. This reaction proceeds with a range of each of these three substrates, providing a method to generate families of pyrroles in high yield. Mechanistic studies suggest this process proceeds via the generation of imino analogues of munchnones, which can undergo in situ coupling with alkynes to liberate isocyanate and form the pyrrole product.

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