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溴乙腈为氰基源的喹喔啉-2(1H)-酮C3位高效氰基化反应研究

Regioselective cyanide of quinoxaline-2(1H)-one (C3) with bromoacetonitrile as the cyanide source

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【作者】 周逸炜聂俊琦

【Author】 ZHOU Yiwei;NIE Junqi;College of Chemistry and Chemical Engineering, Hubei University;

【通讯作者】 聂俊琦;

【机构】 湖北大学化学化工学院

【摘要】 喹喔啉-2(1H)-酮是一类具有独特结构的含氮有机化合物,因其天然存在的生物活性和显著的药用价值,在农药、医药、化工及材料科学等领域展现出广泛的应用前景。近年来,可见光驱动的光氧化还原催化技术在温和条件下已成为构建喹喔啉-2(1H)-酮衍生物的有效策略。本研究实现了在无金属催化剂参与的情况下,以廉价易得的溴乙腈作为氰基来源,通过光催化体系对喹喔啉-2(1H)-酮进行区域选择性C—H氰基化反应,为C—CN键的构筑提供了新颖且可持续的方法。该方法在温和反应条件下顺利进行,能够以中等至优异的产率获得多种3-氰基喹喔啉-2(1H)-酮衍生物,同时表现出良好的官能团兼容性。

【Abstract】 Quinolizine-2(1H)-one is a class of nitrogen-containing organic compounds with unique structures. Due to its natural biological activity and significant medicinal value, it has shown extensive application prospects in the fields of pesticides, medicine, chemical industry, and materials science. In recent years, visible light-driven photo-redox catalytic technology has become an effective strategy for constructing derivatives of quinolizine-2(1H)-one under mild conditions. This study achieved a region-selective C—H cyanation reaction of quinolizine-2(1H)-one using a photo-catalytic system without the participation of metal catalysts, with bromoacetonitrile as the source of the cyano group. This result provided a novel and sustainable method for the construction of C—CN bonds. The method proceeds smoothly under mild reaction conditions and can obtain various 3-cyanomethyl quinolizine-2(1H)-one derivatives with medium to excellent yields, while showing good functional group compatibility.

【基金】 湖北省功能化学品工程技术研究中心开放课题(GCZX-2022-08)资助
  • 【文献出处】 湖北大学学报(自然科学版) ,Journal of Hubei University(Natural Science) , 编辑部邮箱 ,2026年04期
  • 【分类号】O626
  • 【下载频次】7
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