Copper-catalyzed rapid C–H nitration of 8-aminoquinolines by using sodium nitrite as the nitro source under mild conditions. Issue 92 (20th September 2016)

• Record Type: Journal Article
• Authors: Zhu, Xiaolei; Qiao, Li; Ye, Pingping; Ying, Beibei; Xu, Jun; Shen, Chao; Zhang, Pengfei
• Is Part Of: RSC advances. Volume 6:Issue 92(2016)
• Page Start: 89979
• Page End: 89983
• Publication Date: 2016-09-20
• Subjects: Chemistry -- Periodicals; 540.5
• DOI: 10.1039/c6ra19583k
• Languages: English
• ISSNs: 2046-2069

Abstract

Abstract : We report the first example of copper(ii ) catalyzed remote C–H nitration of 8-aminoquinoline amides by using sodium nitrite as nitration reagent under mild conditions in 1 minute which undergoes single electron process. 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.