o-Nitroaniline derivatives. Part II. Reactions of nucleophiles with N-benzylidene-o-nitroaniline

Abstract

The reactions of a range of nucleophiles with N-benzylidene-o-nitroaniline (II) are reported. Reactions involving nucleophiles in which the nucleophilic centre is attached to one hydrogen atom involve addition to the CN group and lead to products such as N-[α-(N-methylanilino)benzyl]-o-nitroaniline (IV) and the α-p-tolylthio-analogue (V). If the nucleophilic centre carries two hydrogen atoms, the addition may be followed by elimination of o-nitroaniline from the adduct. 1-Hydroxy-2-phenylbenzimidazole is formed in high yield by the reaction of N-benzylidene-o-nitroaniline with potassium cyanide in methanol.