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Synthesis of 2-aryl-4-chloropyrroles via ring expansion of 2-aryl-1-chlorocyclopropanecarbaldehydes

Authors
Journal
Tetrahedron
0040-4020
Publisher
Elsevier
Publication Date
Volume
61
Issue
11
Identifiers
DOI: 10.1016/j.tet.2005.01.087
Keywords
  • Ring Expansion
  • Pyrroles
  • Cyclopropanes
Disciplines
  • Biology

Abstract

Abstract An efficient electrophile-induced ring opening of 2-aryl-1-chlorocyclopropanecarbaldehydes is described towards halogenated butanals, which were converted to the corresponding imines. These α,α,γ-trichloroimines proved to be good substrates for a nucleophile-induced ring closure towards 2-pyrrolines as versatile synthons for the synthesis of pyrroles bearing physiologically interesting substitution patterns.

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