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

Carbophilic addition on (and/or sodium borohydride reduction of) an imide ester functionality (3) proceeds with extremely high regioselectivety to produce bifunctionalized hydroxy-omega -carbinol lactam products (4) and (8). These species could act as N-acyliminium ion precursors and, via an O-catio...

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Bibliographic Details
Published inHeterocycles Vol. 54; no. 1; pp. 275 - 282
Main Authors Mamouni, A, Daich, A, Marchalin, S, Decroix, B
Format Journal Article
LanguageEnglish
Published OXFORD Elsevier 01.01.2001
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
cationic cyclization
azepine
N-acyliminium ion
REDUCTION
[1,3]oxazepine
regioselective reduction
DERIVATIVES
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Summary:Carbophilic addition on (and/or sodium borohydride reduction of) an imide ester functionality (3) proceeds with extremely high regioselectivety to produce bifunctionalized hydroxy-omega -carbinol lactam products (4) and (8). These species could act as N-acyliminium ion precursors and, via an O-cationic or pi -cationic cyclization, and they led regioselectively in high yields to fused triheterocyclic azepine (11) or [1,3]oxazepine (18).
ISSN:0385-5414
DOI:10.3987/com-00-s(i)29