Regio- and Chemoselective Mono- and Bisnitration of 8-Amino quinoline Amides with Fe(NO3)3·9H2O as Promoter and Nitro Source

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• 作者：Yan He ; Ningning Zhao ; Liqi Qiu ; Xinying Zhang ; Xuesen Fan
• 刊名：Organic Letters
• 出版年：2016
• 出版时间：December 2, 2016
• 年：2016
• 卷：18
• 期：23
• 页码：6054-6057
• 全文大小：452K
• ISSN：1523-7052

文摘

An efficient and regioselective remote C(5)–H nitration of 8-aminoquinoline amides by using the economical and nontoxic Fe(NO<sub>3sub>)<sub>3sub>·9H<sub>2sub>O as promoter and nitro source has been developed. Furthermore, when CuCl<sub>2sub>·2H<sub>2sub>O was used as a catalyst, 8-aminoquinoline amides dominantly underwent bisnitration to give 5,7-dinitro-8-aminoquinoline amides. Notably, this is the first example in which Fe(NO<sub>3sub>)<sub>3sub>·9H<sub>2sub>O plays a dual role as both chelating promoter and nitration reagent, and CuCl<sub>2sub>·2H<sub>2sub>O acts as an efficient catalyst for the bisnitration of quinolines.