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Paper | Regular issue | Vol 68, No. 6, 2006, pp.1121-1138
Published online, 11th April, 2006
DOI: 10.3987/COM-06-10690
Facile Synthesis of 2-Arylpyrroles from 4-Oxo-butanoic Acids and Their Use in the Preparation of Bis(pyrrolyl)methanes

David J. Jones and Vernon C. Gibson*

*Imperial College London, Exhibition Road, London, SW7 2AZ, U.K.

Abstract

A range of 3-aroyl-propionic acids have been cyclised to unsaturated lactones which, upon reduction using DIBAL-H and reaction with an ammonia source, gave 2-arylpyrroles (Ar = Ph, 1-naphthyl, o-phenoxyphenyl and 4-methyl-2-methylsulfanylphenyl) in excellent yields. Reaction of 2,6-disubstituted aroylpropanals (Ar = 2,4,6-Me3C6H2, anthracenyl and 2-Me-naphthalen-1-yl) with an ammonia source failed to generate pyrroles. The arylpyrroles react readily with ketones or aldehydes in ethanol or under eutectic mix melt conditions to give bis-(pyrrolyl)methanes in excellent isolated yields.