title: Chemoselective Alkylation for Diversity-Oriented Synthesis of 1,3,4-Benzotriazepin-2-ones and Pyrrolo[1,2][1,3,4]benzotriazepin-6-ones, Potential Turn Surrogates.
abstract: 1,3,4-Benzotriazepin-2-ones garner interest for medicinal applications, in part due to their relationship with benzodiazepinones. Ten 1,3,4-benzotriazepin-2-ones 6 and 19 and six pyrrolo[1,2][1,3,4]benzotriazepin-6-ones 7 and 23 were prepared in four to seven steps and 4-60% overall yields by a divergent strategy from methyl anthranilate employing chemoselective alkylations of common linear and cyclic precursors to diversify three triazepinone ring positions (N1, N3, and C5). X-ray crystallography demonstrated that benzotriazepinone 19g may serve as a γ-turn mimic.
authors.affiliation: Département de Chimie, Université de Montréal , C.P. 6128, Succursale Centre-Ville, Montréal H3C 3J7, Canada.
authors.forename: Antoine
authors.initials: A
authors.lastname: Douchez
authors.affiliation: Département de Chimie, Université de Montréal , C.P. 6128, Succursale Centre-Ville, Montréal H3C 3J7, Canada.
authors.forename: William D
authors.initials: WD
authors.lastname: Lubell
mesh_terms: D000478:Alkylation; D001381:Azepines / Q000737:chemistry; D001570:Benzodiazepinones / Q000138:chemical synthesis* / Q000737:chemistry; D018360:Crystallography, X-Ray; D008968:Molecular Conformation; D015394:Molecular Structure
chemical_list: D001381:Azepines; D001570:Benzodiazepinones; C401522:triazepinone