N-Aminations of Benzylamines and Alicyclic Amines with Nitrosoarenes to Hydrazones and Hydrazides

Abstract

Unlike other alkylamines, benzylamines upon reaction with a nitrosoarene undergo oxidation to the corresponding imines. A direct amination of benzylamines, which was difficult to achieve due to its facile oxidation, to the corresponding hydrazones is reported. A wide variety of benzylamines and N-heterocycles were reacted with nitrosoarenes to provide structurally diverse hydrazones and hydrazides, respectively. Moreover, the direct N-amination reaction was applied to the one-pot synthesis of triazoles.