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Synthesis 2011(3): 480-484  
DOI: 10.1055/s-0030-1258377
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

New Access to 5-Substituted 1,3-Benzothiazol-2(3H)-ones and Their N-Methyl Analogues by a Palladium Coupling Reaction

Céline Pirata, Vincent Ultréb, Nicolas Lebeguea, Pascal Berthelota, Saïd Yousa, Pascal Carato*a
a Faculté de Pharmacie, Laboratoire de Chimie Thérapeutique (EA 4481), Université Lille Nord de France, 3 rue du Professeur Laguesse, BP 83, 59006 Lille Cedex, France
e-Mail: pascal.carato@univ-lille2.fr; Fax: +3(33)20959009;
b Faculté de Pharmacie, LARMN, Université Lille Nord de France, 3 rue du Professeur Laguesse, BP 83, 59006 Lille Cedex, France
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Publication History

Received 18 October 2010
Publication Date:
20 December 2010 (online)

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Abstract

5-Substituted 1,3-benzothiazol-2(3H)-ones and their N-methyl analogues were readily prepared from the corresponding 5-bromo-1,3-benzothiazol-2(3H)-ones by means of Stille and Suzuki reactions. The compounds were substituted at the C-5 position with vinyl, acyl, or aryl groups optionally carrying electron-withdrawing or electron-donating substituents.

Key words

heterocycles - coupling - catalysis - benzothiazolones - Stille reaction

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