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Synthesis 2019; 51(13): 2687-2696
DOI: 10.1055/s-0037-1610701
DOI: 10.1055/s-0037-1610701
special topic
N-Aminations of Benzylamines and Alicyclic Amines with Nitrosoarenes to Hydrazones and Hydrazides
We acknowledge financial support from Science and Engineering Research Board (SERB).Further Information
Publication History
Received: 13 February 2019
Accepted after revision: 12 March 2019
Publication Date:
17 April 2019 (online)
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.
Supporting Information
- Supporting information for this article is available online at https://doi.org/10.1055/s-0037-1610701. X-ray data and copies of NMR spectra are included.
- Supporting Information
- CIF File
-
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Aromatic N-amination using other reagents, see:
For related oxidation of cyclic amines, see: