Heteroaromatic Decarboxylative Claisen Rearrangement Reactions

Donald Craig; N. Paul King; Jörg T. Kley; David M. Mountford

doi:10.1055/s-2005-918448

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Heteroaromatic Decarboxylative Claisen Rearrangement Reactions

Donald Craig*^a, N. Paul King^b, Jörg T. Kley^c, David M. Mountford^a
^a Department of Chemistry, Imperial College London, South Kensington Campus, London SW7 2AZ, UK
Fax: +44(20)75945868; e-Mail: d.craig@imperial.ac.uk;
^b Neurology and GI Centre of Excellence for Drug Discovery, GlaxoSmithKline Research Limited, New Frontiers Science Park, Third Avenue, Harlow, Essex CM19 5AW, UK
^c Department of Chemical Research, Boehringer Ingelheim Pharma GmbH & Co. KG, Birkendorfer Strasse 65, 88397 Biberach an der Riss, Germany

Abstract

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Abstract

Furan-2-ylmethyl, thien-2-ylmethyl and pyrrol-2-ylmethyl tosylacetates undergo facile decarboxylative Claisen rearrangement upon exposure to N,O-bis(trimethylsilyl)acetamide-potassium acetate to yield the corresponding 2,3-disubstituted heteroaromatic products in good yield. However, for 1-(thien-2-yl)ethyl tosylacetates and substrates derived from 3-(hydroxyalkyl)indoles rearomatisation does not occur.

Key words

heterocycles - heterogenous catalysis - pericyclic reactions - sulfones - tautomerism

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References

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