Publication: Unlocking the synthetic potential of aziridine and cyclopropane-fused quinolin-2-ones by regioselective fragmentation of its three-membered rings
Authors
Diaz, Javier ; Rodenas, Daniel ; Ballester, Francisco J ; Alajarín, Mateo ; Orenes, Raul A. ; Sanchez-Andrada, Pilar ; Vidal, Angel
item.page.secondaryauthor
item.page.director
Publisher
Elsevier
publication.page.editor
publication.page.department
DOI
10.1016/j.arabjc.2018.07.002
item.page.type
info:eu-repo/semantics/article
Description
Abstract
The cyclization of cis-2-(2-azidophenyl)-1-benzyl-3-ethoxycarbonylaziridines and trans-2-(2-azidophenyl)-3-nitrocyclopropane-1,1-dicarboxylates yielded the respective aziridino[2,3-c]quinolin-2-ones and cyclopropa[c]quinolin-2-ones. Ring-opening of the aziridine-fused species under silica gel catalysis provided 3-aminoquinolin-2-ones whereas the ring-expansion of the cyclopropane-fused derivatives by the action of sodium hydride gave 1-benzazepin-2-ones, in both cases in a regioselective manner. A computational study using DFT methods revealed that the mechanism for the transformation of cyclopropa[c]quinolin-2-ones into 1-benzazepin-2-ones involves the initial deprotonation step of its amide function followed by two pericyclic events: a 6π-electrocyclic ring opening and a subsequent [1,5]-H shift.
publication.page.subject
Citation
Arabian Journal of Chemistry (2020) 13, 2702–2714.
item.page.embargo
Collections
Ir a Estadísticas
Sin licencia Creative Commons.