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Friedel-Crafts chemistry. Part 45: expedient new improved process for the synthesis of oxacarbazepine precursor 10,11-dihydro-10-oxo- 5H-dibenz(b,f)azepine via Friedel-Crafts cycliacylations

An unprecedented efficient methodology for the synthesis of 10,11-dihydro-10-oxo-5H- dibenz(b,f)azepine via a three new synthetic pathways is described. The key steps of this approach are based on classical Friedel-Craft ring closures of three precursors 1-(2-(N-phenyl-N- tosylamino)phenyl)-2-bromoethanone, ethyl 2-(2-(N-phenyl-N-tosylamino)phenyl)acetate or 2- (2-(N-phenyl-N-tosylamino)phenyl)acetic acid, by using AlCl3/CH3NO2 or AlCl3 in dichloromethane. For the latter two precursors, P2O5 in toluene worked also well. The precursors were easily obtained in a two- or three -step reaction sequence. Overall, the described approach allows easy and efficient access to the tricyclic dibenzoazepinone ring system from easily accessible starting materials.