Tetrahedron p. 3535 - 3542 (1980)
Update date:2022-07-30
Topics:
Henichart, J. P.
Bernier J. L.
Vaccher, C.
Houssin, R.
Warin, V.
Baert, F.
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 SNAr 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.
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