Selective synthesis of β-nitrated N-heterocycles and N-nitroso-2-alkoxyamine aldehydes from inactivated cyclic amines promoted by tBuONO and oxoammonium salt

Yan He; Zhi Zheng; Yajie Liu; Jiajie Qiao; Xinying Zhang; Xuesen Fan

doi:10.1039/C9CC05963F

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Selective synthesis of β-nitrated N-heterocycles and N-nitroso-2-alkoxyamine aldehydes from inactivated cyclic amines promoted by ^tBuONO and oxoammonium salt†

Yan He,

*^a Zhi Zheng,^a Yajie Liu,^a Jiajie Qiao,^a Xinying Zhang

^a and Xuesen Fan

*^a

Author affiliations

* Corresponding authors

^a Henan Key Laboratory of Organic Functional Molecules and Drug Innovation, Key Laboratory for Yellow River and Huai River Water Environmental Pollution Control, Ministry of Education, Collaborative Innovation Center of Henan Province for Green Manufacturing of Fine Chemicals, School of Environment, School of Chemistry and Chemical Engineering, Henan Normal University, Xinxiang, Henan 453007, China
E-mail: heyan@htu.cn, xuesen.fan@htu.cn

Abstract

A convenient synthesis of β-nitrated tetrahydropyridines has been successfully realized via dehydrogenative β-C–H nitrification of N-arylpiperidines promoted by ^tBuONO and the oxoammonium salt in THF. In addition, changing the solvent to an acetone/water mixture resulted in selective cleavage and tunable functionalization of the inert C–N bonds in cyclic amines to afford N-nitroso chain 2-alkoxyamine aldehydes. Notably, the application of N-nitroso-2-alkoxyamine aldehydes was showcased by their efficient transformation into 4-substituted 1,2-diazepines featuring a facile construction of a seven-membered ring.

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Article information

DOI: https://doi.org/10.1039/C9CC05963F
Article type: Communication
Submitted: 31 Jul 2019
Accepted: 19 Sep 2019
First published: 20 Sep 2019

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Chem. Commun., 2019,55, 12372-12375

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Selective synthesis of β-nitrated N-heterocycles and N-nitroso-2-alkoxyamine aldehydes from inactivated cyclic amines promoted by ^tBuONO and oxoammonium salt

Y. He, Z. Zheng, Y. Liu, J. Qiao, X. Zhang and X. Fan, Chem. Commun., 2019, 55, 12372 DOI: 10.1039/C9CC05963F

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Chemical Communications