Issue 4, 2001
From the journal:

Journal of the Chemical Society, Perkin Transactions 1

Selective vicarious nucleophilic amination of 3-nitropyridines

Jan M. Bakke,*a   Harald Svensena  and  Raffaela Trevisana  

* Corresponding authors

a Department of Chemistry, Norwegian University of Science and Technology, Sem Sælands vei 8, Trondheim, Norway

Abstract

Nine 3-nitropyridine compounds and 4-nitroisoquinoline have been aminated in the 6-position (for 4-nitroisoquinoline in the 1-position) by vicarious nucleophilic substitution reactions. Two amination reagents were used, hydroxylamine and 4-amino-1,2,4-triazole. The yields were from moderate to good. Use of hydroxylamine gave an easy work-up procedure by which almost pure product was obtained directly, but 4-amino-1,2,4-triazole gave better yields of the aminated product for some of the substrates. By this, a general method for the preparation of 3- or 4-substituted-2-amino-5-nitropyridines was obtained.

Graphical abstract: Selective vicarious nucleophilic amination of 3-nitropyridines

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Article information

DOI
https://doi.org/10.1039/B008660F
Article type
Paper
Submitted
26 Oct 2000
Accepted
22 Dec 2000
First published
24 Jan 2001

J. Chem. Soc., Perkin Trans. 1, 2001, 376-378

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Selective vicarious nucleophilic amination of 3-nitropyridines

J. M. Bakke, H. Svensen and R. Trevisan, J. Chem. Soc., Perkin Trans. 1, 2001, 376 DOI: 10.1039/B008660F

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