Evaluation of N??hydroxymethylphthalimide in alkaline medium: Novel entry to the tricyclic [1, 3] oxazepine core via an intramolecular π and O??cationic cyclization
…, A Pesquet, A Daïch, A Chihab??Eddine…
Index: Cul, Armelle; Chihab-Eddine, Abderrahim; Pesquet, Anthony; Marchalin, Stefan; Daich, Adam Journal of Heterocyclic Chemistry, 2003 , vol. 40, # 3 p. 499 - 505
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Citation Number: 9
Abstract
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.
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