A 'Classical' approach to the synthesis of perloline
- 1 January 1983
- journal article
- research article
- Published by CSIRO Publishing in Australian Journal of Chemistry
- Vol. 36 (7) , 1455-1467
- https://doi.org/10.1071/ch9831455
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.Keywords
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