1. Rearrangement of N-Aryl-2-Vinylaziridines to Benzoazepines and Dihydropyrroles: A Synthetic and Theoretical Study
- Author
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Nazzareno Re, Simone Fantauzzi, Emma Gallo, Fabio Ragaini, Cristiana Piangiolino, Alessandro Caselli, and Sergio Cenini
- Subjects
Azides ,Reaction mechanism ,Aryl ,Organic Chemistry ,Molecular Conformation ,chemistry.chemical_element ,Homogeneous catalysis ,General Chemistry ,Catalysis ,Ruthenium ,chemistry.chemical_compound ,Isomerism ,Models, Chemical ,chemistry ,Heterocyclic Compounds ,Computational chemistry ,Organic chemistry ,Pyrroles - 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.
- Published
- 2008
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