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Synthesis 2004(16): 2736-2742
DOI: 10.1055/s-2004-831244
DOI: 10.1055/s-2004-831244
PAPER
© Georg Thieme Verlag Stuttgart · New YorkSilica-Assisted Reactions of Pyrroles with 1-Acyl-2-bromoacetylenes
Weitere Informationen
Received
28 June 2004
Publikationsdatum:
22. September 2004 (online)
Publikationsverlauf
Publikationsdatum:
22. September 2004 (online)
Abstract
Pyrroles react with 1-acyl-2-bromoacetylenes at room temperature on silica to give 2-acyl-1,1-di(pyrrol-2-yl)ethenes as major products in yields of up to 60%. Under reaction conditions employed, the intermediates (E)-2-(2-acyl-1-bromoethenyl)pyrroles (3-11% isolated yields) either readily exchange the bromine atom for the pyrrole molecule or eliminate HBr to afford 2-(2-acylethynyl)pyrroles, which can be isolated in 9-22% yields by chromatography of the reaction mixture on Al2O3.
Key words
pyrroles - 1-acyl-2-bromoacetylenes - 2-(2-acyl-1-bromoethenyl)pyrroles - 2-acyl-1,1-di(pyrrol-2-yl)ethenes - 2-(2-acylethynyl)pyrroles - silica
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