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

Anisha Purkait; Chandan K. Jana

doi:10.1055/s-0037-1610701

Synthesis, Table of Contents

Synthesis 2019; 51(13): 2687-2696
DOI: 10.1055/s-0037-1610701

special topic

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

Anisha Purkait

,

Chandan K. Jana *

Department of Chemistry, Indian Institute of Technology Guwahati, Guwahati 781039, India Email: ckjana@iitg.ac.in

› Author Affiliations

Abstract

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Published as part of the Special Topic Amination Reactions in Organic Synthesis

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.

Key words

N-amination - hydrazones - nitrosoarenes - triazoles - benzylamines

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References

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