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Communication | Special issue | Vol 64, No. 1, 2004, pp.33-39
Published online, 17th September, 2004
DOI: 10.3987/COM-04-S(P)18
Access to the Newly Isoindolo[1,3]benzothiazocinones via the Combination of N-Acyliminium Chemistry and Friedel-Crafts Type π-Cyclization

Armelle Cul, Adam Daïch,* Bernard Decroix, Gérard Sanz, and Luc Van Hijfte

*Laboratoire de Chimie, URCOM, Faculté des Sciences et Techniques, Université du Havre, 25 Rue Philippe Lebon, B.P. 540 76058 Le Havre Cedex, France

Abstract

New racemic and chiral [4,2]- and [3,5]benzothiazocines (4) and (5) in the isoindolinone series were synthesized easily in few steps based on the combination of N-acyliminium chemistry and π-cationic cyclization of acylium ions. The chemoselectivity observed during these processes, particularly in the reduction, the thioalkylation and the cyclization stages, were also discussed.