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Evaluation of N‐hydroxymethylphthalimide in alkaline medium: Novel entry to the tricyclic [1,3]oxazepine core via an intramolecular π and O‐cationic cyclization

Identifieur interne : 000E51 ( France/Analysis ); précédent : 000E50; suivant : 000E52

Evaluation of N‐hydroxymethylphthalimide in alkaline medium: Novel entry to the tricyclic [1,3]oxazepine core via an intramolecular π and O‐cationic cyclization

Auteurs : Armelle Cul [France] ; Anthony Pesquet [France] ; Adam Daïch [France] ; Abderrahim Chihab-Eddine [Maroc] ; Štefan Marchalín [Slovaquie]

Source :

RBID : ISTEX:7BEF34D898D7FD27B9C36C9CE81F80E3FB784F64

Abstract

Fused isoindolo[1,3]benzo(or thieno)oxazepines 8a,b and one of their positional isomers aromatic tricyclic N,O‐acetals 13b are reported to occur efficiently in a three‐step sequence from N‐hydroxy‐methylphthalimide (6). The key step of this methodology is the intramolecular arylation of an endocyclic and/or exocyclic N‐acyliminium cation. The mechanism leading to these species, in particular to a tricyclic lactam 13b, is discussed.

Url:
DOI: 10.1002/jhet.5570400314


Affiliations:


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ISTEX:7BEF34D898D7FD27B9C36C9CE81F80E3FB784F64

Le document en format XML

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