Synthesis of 2-aryl-4-chloropyrroles via ring expansion of 2-aryl-1-chlorocyclopropanecarbaldehydes |
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Authors: | Guido Verniest |
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Affiliation: | Department of Organic Chemistry, Faculty of Bioscience Engineering, Ghent University, Coupure Links 653, B-9000 Ghent, Belgium |
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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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Keywords: | Ring expansion Pyrroles Cyclopropanes |
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