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.
Rearrangement of N-Aryl-2-Vinylaziridines to Benzoazepines and Dihydropyrroles: A Synthetic and Theoretical Study / S. Fantauzzi, E. Gallo, A. Caselli, C. Piangiolino, F. Ragaini, N. Re, S. Cenini. - In: CHEMISTRY-A EUROPEAN JOURNAL. - ISSN 0947-6539. - 15:5(2009), pp. 1241-1251.
Rearrangement of N-Aryl-2-Vinylaziridines to Benzoazepines and Dihydropyrroles: A Synthetic and Theoretical Study
S. FantauzziPrimo
;E. GalloSecondo
;A. Caselli;C. Piangiolino;F. Ragaini;S. CeniniUltimo
2009
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.File | Dimensione | Formato | |
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