title: Desulfonylative radical ring closure onto aromatics. A modular route to benzazepin-2-ones and 5-arylpiperidin-2-ones.
abstract: Adducts from the intermolecular radical addition of N-xanthylacetyl-N-methanesulfanilides to Boc-protected allylamine undergo ring closure with loss of a methanesulfonyl radical to give benzazepin-2-ones. Upon deprotection and exposure to triethylamine, these compounds rearrange into 5-aryl-2-piperidones. This approach also represents a useful route to benzazepin-2-ones unsubstituted on the nitrogen atom of the azepinone ring.
authors.affiliation: Laboratoire de Synthèse Organique, CNRS UMR 7652 Ecole Polytechnique, 91128 Palaiseau Cedex, France.
authors.forename: Nicolas
authors.initials: N
authors.lastname: Charrier
authors.forename: Zhibo
authors.initials: Z
authors.lastname: Liu
authors.forename: Samir Z
authors.initials: SZ
authors.lastname: Zard
mesh_terms: D000499:Allylamine / Q000737:chemistry*; D001552:Benzazepines / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003500:Cyclization; D015394:Molecular Structure; D009584:Nitrogen / Q000737:chemistry; D010881:Piperidones / Q000138:chemical synthesis* / Q000737:chemistry
chemical_list: D001552:Benzazepines; D010881:Piperidones; D000499:Allylamine; D009584:Nitrogen