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Communication | Special issue | Vol 76, No. 2, 2008, pp.1017-1022
Published online, 26th May, 2008
DOI: 10.3987/COM-08-S(N)97
An Easy Access to the Exocyclic Lactams Analogous of the Central Nervous System Active Tricyclic Nitroxapine, Mianserine and Chlothiapine Agents Using N-Acyliminium Chemistry

Abderrahmane Hadou, Abdulkareem Hamid, Hilarion Mathouet, Mohamed-Fadel Deïda, and Adam Daïch*

*URCOM, EA 3221, UFR of Sciences & Techniques, University of Le Havre, BP 540, 25 rue Philippe Lebon, F-76058 Le Havre Cedex, France

Abstract

The conformationally restrained dibenzothia(oxa)zepines and dibenzazepines 4-6 analogous to the antidepressant Sintamil® were prepared easily by π-cationic cyclization of the N-acyliminium ions 9A-C precursors with neat trifluoroacetic acid in three step-sequence starting from available amines and anhydrides. The regioselectivity in the reduction of imides especially in the maleimide derivatives as well as in the cyclization step was also discussed.