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Issue 6, 2013
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[5C + 1N] Annulation of 2,4-pentadienenitriles with hydroxylamine: a synthetic route to multi-substituted 2-aminopyridines

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Abstract

A facile and efficient synthetic route to multi-substituted 2-aminopyridines has been developed via a formal [5C + 1N] annulation of readily available 2,4-pentadienenitriles with hydroxylamine (NH2OH) under very mild conditions, which involves sequential intermolecular aza-nucleophilic addition of hydroxylamine, intramolecular aza-cyclization, and dehydration reactions.

Graphical abstract: [5C + 1N] Annulation of 2,4-pentadienenitriles with hydroxylamine: a synthetic route to multi-substituted 2-aminopyridines

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Article information


Submitted
21 Oct 2012
Accepted
06 Dec 2012
First published
07 Dec 2012

Org. Biomol. Chem., 2013,11, 1001-1006
Article type
Paper

[5C + 1N] Annulation of 2,4-pentadienenitriles with hydroxylamine: a synthetic route to multi-substituted 2-aminopyridines

X. Xin, P. Huang, D. Xiang, R. Zhang, F. Zhao, N. Zhang and D. Dong, Org. Biomol. Chem., 2013, 11, 1001
DOI: 10.1039/C2OB27053F

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