Abstract An approach to the synthesis of perloline by the reaction of (2-bromophenyl)(3', 4'- dimethoxy-phenyl) amine with a suitably 4-substituted 2-oxo-1, 2-dihydropyridine-3- carboxylic acid was unsuccessful due to the inability to form the amide bond. The diphenylamine was efficiently synthesized from the nitrone of dimethoxybenzylidene-2- bromoaniline via the oxaziridine, the thermal rearrangement of which was investigated. ...