1. Access to the New Isoindolo[1,3]benzothiazocinones via the Combination of N-Acyliminium Chemistry and Friedel—Crafts Type π-Cyclization
- Author
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Hucher, Nicolas, Pesquet, Anthony, Netchitaïlo, Pierre, Daïch, Adam, Cul, Armelle, Decroix, Bernard, Sanz, Gérard, Van Hijfte, Luc, Unité de Recherche en Chimie Organique et Macromoléculaire (URCOM), Université Le Havre Normandie (ULH), Normandie Université (NU)-Normandie Université (NU), and Normandie Université (NU)
- Subjects
Pharmacology ,[CHIM.ORGA]Chemical Sciences/Organic chemistry ,010405 organic chemistry ,Chemistry ,Organic Chemistry ,[CHIM.CATA]Chemical Sciences/Catalysis ,[CHIM.THER]Chemical Sciences/Medicinal Chemistry ,General Medicine ,010402 general chemistry ,Medicinal chemistry ,01 natural sciences ,Combinatorial chemistry ,Analytical Chemistry ,3. Good health ,0104 chemical sciences ,Computational chemistry ,Stereoselectivity ,Chemoselectivity ,Friedel–Crafts reaction ,ComputingMilieux_MISCELLANEOUS - 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.
- Published
- 2005