ACCES AUX DINITRO-2,4 DIARYLAMINES PAR SUBSTITUTION NUCLEOPHILE SNAr-LIMITES DE LA REACTION ET APPLICATION A LA SYNTHESE DE CYANOCARBAZOLES

Article abstract of DOI:10.1016/0040-4020(80)88049-5

3-Cyanocarbazoles, key-intermediates in the total synthesis of pyrido <4,3-b> carbazoles, have been obtained starting from easily available materials and involving the cyclization of diarylamines.The first step of the preparation consists in a S_NAr reaction between a para substituted aniline and a chloro- (or bromo)-dinitrobenzene.This nucleophilic substitution has been found to be hindered by the steric effect of a methyl group, explained in terms of inhibition of resonance and confirmed by X-ray determination.