Issue 21, 2004
From the journal:

Chemical Communications

Dearomatising rearrangements of lithiated thiophenecarboxamides†

Jonathan Clayden,*a   Rachel Turnbull,a   Madeleine Helliwella  and  Ivan Pintob  

* Corresponding authors

a Department of Chemistry, University of Manchester, Oxford Road, Manchester, UK
E-mail: j.p.clayden@man.ac.uk

b GlaxoSmithKline Medicines Research Centre, Gunnels Wood Road, Stevenage, Herts, UK

Abstract

Thiophene-3-carboxamides bearing allyl or benzyl substituents at nitrogen undergo dearomatising cyclisation on treatment with LDA. Rearrangements transform the dearomatised products into pyrrolinones, azepinones or partially saturated azepinothiophenes.

Graphical abstract: Dearomatising rearrangements of lithiated thiophenecarboxamides

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Article information

DOI
https://doi.org/10.1039/B409150G
Article type
Communication
Submitted
17 Jun 2004
Accepted
13 Aug 2004
First published
22 Sep 2004

Chem. Commun., 2004, 2430-2431

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Dearomatising rearrangements of lithiated thiophenecarboxamides

J. Clayden, R. Turnbull, M. Helliwell and I. Pinto, Chem. Commun., 2004, 2430 DOI: 10.1039/B409150G

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