Azepine and [1,3]oxazepine fused ring construction through a cationic cyclization: An N-acyliminium ion trapping of an oxygen atom or olefin

Authors
Mamouni, A Daich, A Marchalin, S Decroix, B
Citation
A. Mamouni et al., Azepine and [1,3]oxazepine fused ring construction through a cationic cyclization: An N-acyliminium ion trapping of an oxygen atom or olefin, HETEROCYCLE, 54(1), 2001, pp. 275-282
Citations number
16
Categorie Soggetti
Organic Chemistry/Polymer Science
Journal title
HETEROCYCLES
ISSN journal
03855414 → ACNP
Volume
54
Issue
1
Year of publication
2001
Pages
275 - 282
Database
ISI
SICI code
0385-5414(20010101)54:1<275:AA[FRC>2.0.ZU;2-M
Abstract
Carbophilic addition on (and/or sodium borohydride reduction of) an imide e ster functionality (3) proceeds with extremely high regioselectivety to pro duce bifunctionalized hydroxy-omega -carbinol lactam products (4) and (8). These species could act as N-acyliminium ion precursors and, via an O-catio nic or pi -cationic cyclization, and they led regioselectively in high yiel ds to fused triheterocyclic azepine (11) or [1,3]oxazepine (18).