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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
Author(s) -
Cul Armelle,
Pesquet Anthony,
Daïch Adam,
ChihabEddine Abderrahim,
Marchalín Štefan
Publication year - 2003
Publication title -
journal of heterocyclic chemistry
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.321
H-Index - 59
eISSN - 1943-5193
pISSN - 0022-152X
DOI - 10.1002/jhet.5570400314
Subject(s) - chemistry , tricyclic , intramolecular force , cationic polymerization , stereochemistry , core (optical fiber) , combinatorial chemistry , organic chemistry , materials science , composite material
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.