title: Rearrangement of N-aryl-2-vinylaziridines to benzoazepines and dihydropyrroles: a synthetic and theoretical study.
abstract: Herein we report the one-pot synthesis of several N-heterocyclic compounds by rearrangement reactions of N-aryl-2-vinylaziridines. The optimization of the synthetic methodology employed allowed us to obtain differently substituted 2,5-dihydro-1H-benzo[b]azepines in good yields and purities. The relationship between the nature of the starting N-aryl-2-vinylaziridine and the obtained N-heterocycle was also investigated. Finally, to rationalize all the experimental results reported in this paper a theoretical study was performed that casts light on the reaction mechanism.
authors.affiliation: Dipartimento di Chimica Inorganica, Metallorganica e Analitica Lamberto Malatesta, Università degli Studi di Milano and ISTM-CNR, Via Venezian 21, I-20133 Milano, Italy.
authors.forename: Simone
authors.initials: S
authors.lastname: Fantauzzi
authors.forename: Emma
authors.initials: E
authors.lastname: Gallo
authors.forename: Alessandro
authors.initials: A
authors.lastname: Caselli
authors.forename: Cristiana
authors.initials: C
authors.lastname: Piangiolino
authors.forename: Fabio
authors.initials: F
authors.lastname: Ragaini
authors.forename: Nazzareno
authors.initials: N
authors.lastname: Re
authors.forename: Sergio
authors.initials: S
authors.lastname: Cenini
mesh_terms: D001386:Azides / Q000138:chemical synthesis* / Q000737:chemistry; D006571:Heterocyclic Compounds / Q000138:chemical synthesis* / Q000737:chemistry; D007536:Isomerism; D008956:Models, Chemical; D008968:Molecular Conformation; D011758:Pyrroles / Q000138:chemical synthesis / Q000737:chemistry
chemical_list: D001386:Azides; D006571:Heterocyclic Compounds; D011758:Pyrroles; C013231:pyrroline