Tetrahedron

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

G Verniest, S Claessens, F Bombeke, T Van Thienen…

Index: Verniest, Guido; Claessens, Sven; Bombeke, Filip; Van Thienen, Tinneke; De Kimpe, Norbert Tetrahedron, 2005 , vol. 61, # 11 p. 2879 - 2887

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Citation Number: 10

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.