Rearrangement of N-aryl-2-vinylaziridines to benzoazepines and dihydropyrroles: a synthetic and theoretical study.
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.
Fantauzzi
Simone
S
Dipartimento di Chimica Inorganica, Metallorganica e Analitica Lamberto Malatesta, Università degli Studi di Milano and ISTM-CNR, Via Venezian 21, I-20133 Milano, Italy.
Gallo
Emma
E
Caselli
Alessandro
A
Piangiolino
Cristiana
C
Ragaini
Fabio
F
Re
Nazzareno
N
Cenini
Sergio
S
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
D001386:Azides; D006571:Heterocyclic Compounds; D011758:Pyrroles; C013231:pyrroline