AZIRIDINATION BY OXIDATIVE ADDITION OF N-AMINOQUINAZOLONES TO ALKENES: EVIDENCE FOR NON-INVOLVEMENT OF N-NITRENES

Article abstract of DOI:10.1016/S0040-4020(01)80116-2

Oxidation of 3-aminoquinazolones e.g. (22) with lead tetra-acetate at -20 deg C gives N-acetoxyaminoquinazolones e.g. (23) which are stable in solution at this temperature.These N-acetoxyaminoquinazolones function as inter- and intramolecular aziridinating agents for alkenes and appear to be playing the role previously ascribed to the corresponding N-nitrenes.An analogous N-acetoxyaminophthalimide intermediate (31) is implicated in the lead tetra-acetate oxidation of N-aminophthalimide (4).