Alkylaminonitrobenzenes by Vicarious Nucleophilic Amination with 4-(Alkylamino)-1,2,4-triazoles

Abstract

A series of 4-(alkylamino)-1,2,4-triazoles transfer the alkylamino group to the 4-position of nitrobenzene and various 3-substituted nitrobenzenes, with no detectable ortho substitution. By contrast 2-nitrothiophene reacts in the 3-position and 2-nitronaphthalene in the 1-position; 1-nitronaphthalene gives a mixture of products derived from dominant 2- with some 4-substitution. The orientations are discussed and rationalized. © 1988, American Chemical Society. All rights reserved.