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Synthesis 2005(19): 3279-3282  
DOI: 10.1055/s-2005-918448
PAPER
© Georg Thieme Verlag Stuttgart · New York

Heteroaromatic Decarboxylative Claisen Rearrangement Reactions

Donald Craig*a, N. Paul Kingb, Jörg T. Kleyc, David M. Mountforda
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
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Publication History

Received 14 September 2005
Publication Date:
27 October 2005 (online)

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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