A 'Classical' approach to the synthesis of perloline

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. Conjugate additions of a diphenylamine dianion to unsaturated esters are reported.