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Note | Regular issue | Vol 71, No. 9, 2007, pp.2041-2047
Published online, 29th May, 2007
DOI: 10.3987/COM-07-11078
Synthesis of 6-Cycloalkylcarbonyl-2(3H)-benzothiazolones via 6-Tributyltin Intermediates

Pascal Carato,* Kallyl Cherry, Nicolas Lebegue, Pascal Berthelot, and Saïd Yous

*Laboratorie de Chimie Thérapeutique, Faculté Pharmcie, Université de Lille 2, 3, rue du Professeur Laguesse, BP 83, 59006 Lille Cedex, France

Abstract

6-Cycloalkylcarbonyl-2(3H)-benzothiazolones cannot be prepared by classical Friedel-Crafts acylation with the corresponding cycloalkylcarbonyl chlorides. We have explored new way via stille coupling from the tributyltin intermediates which were synthesised by protection of the NH group with ethylmethyl ether or potassium salt of the corresponding 6-bromo-2-(3H)-benzothiazolone. The stille coupling reaction of these tributyltin intermediates with the desired cycloalkylcarbonyl chlorides followed by deprotection of the NH group, afforded the corresponding 6-cycloalkylcarbonyl-2(3H)-benzothiazolones.