title: Oxidation of p-aminophenols and formal radical cyclization onto benzene rings: formation of benzo-fused nitrogen heterocycles.
abstract: p-Iodophenol and its O-MOM-protected ether can be converted into iodoamines 2. These give cross-conjugated ketones 3 on oxidation with hypervalent iodides in the presence of methanol, and the ketones undergo radical cyclization. Exposure of the products to acid or sequential treatment with a Grignard reagent and acid effects rearomatization to produce benzo-fused nitrogen heterocycles 4.
authors.affiliation: Chemistry Department, University of Alberta, Edmonton, Alberta, Canada T6G 2G2.
authors.forename: Stephen P
authors.initials: SP
authors.lastname: Fletcher
authors.forename: Derrick L J
authors.initials: DL
authors.lastname: Clive
authors.forename: Jianbiao
authors.initials: J
authors.lastname: Peng
authors.forename: David A
authors.initials: DA
authors.lastname: Wingert