RSC Advances 2016: Nitration of Quinolines

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Paper

Copper-catalyzed rapid C–H nitration of

 8-aminoquinolines by using sodium nitrite

 as the nitro source under mild conditions

Xiaolei Zhu,^a   Li Qiao,^a   Pingping Ye,^a   Beibei Ying,^a   Jun Xu,^a   Chao Shen^b and   Pengfei Zhang*^a  

DOI: 10.1039/C6RA19583K
Received 03 Aug 2016, Accepted 16 Sep 2016
First published online 16 Sep 2016

                               

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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.

                                                                                                                           

                                

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