Issue 92, 2016

Copper-catalyzed rapid C–H nitration of 8-aminoquinolines by using sodium nitrite as the nitro source under mild conditions

Abstract

A mild, rapid and efficient method for copper-catalyzed nitration of quinolines at the C5 or C7 position was reported firstly by using sodium nitrite as the nitro source. A series of nitrated quinoline derivatives were achieved in moderate to good yields via remote C–H activation. The method overcomes some shortcomings reported in previous nitration strategies, such as employing expensive metal catalysts or using toxic and unstable nitrating agents. Furthermore, some of the products can be obtained through filtration which displays the operational simplicity of this methodology. Importantly, this protocol may provide a practical synthetic tool for the introduction of nitro groups into drug molecules.

Graphical abstract: Copper-catalyzed rapid C–H nitration of 8-aminoquinolines by using sodium nitrite as the nitro source under mild conditions

Supplementary files

Article information

Article type
Paper
Submitted
03 Aug 2016
Accepted
16 Sep 2016
First published
16 Sep 2016

RSC Adv., 2016,6, 89979-89983

Copper-catalyzed rapid C–H nitration of 8-aminoquinolines by using sodium nitrite as the nitro source under mild conditions

X. Zhu, L. Qiao, P. Ye, B. Ying, J. Xu, C. Shen and P. Zhang, RSC Adv., 2016, 6, 89979 DOI: 10.1039/C6RA19583K

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