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Discovery of 2-(pyridin-2-yl)aniline as a directing group for the sp2 C–H bond amination mediated by cupric acetate
Organic & Biomolecular Chemistry ( IF 2.9 ) Pub Date : 2017-07-24 00:00:00 , DOI: 10.1039/c7ob01353a
Hong-Yi Zhao 1, 2, 3, 4, 5 , Hui-Yan Wang 1, 2, 3, 4, 5 , Shuai Mao 1, 2, 3, 4, 5 , Minhang Xin 1, 2, 3, 4, 5 , Hao Zhang 1, 2, 3, 4, 5 , San-Qi Zhang 1, 2, 3, 4, 5
Affiliation  

2-(Pyridin-2-yl) aniline was designed as a new, removable directing group in promoting C–H amination mediated by cupric acetate. Employing this auxiliary, the β-C(sp2)–H bonds of benzamide derivatives can be effectively aminated with a variety of amines in moderate to good yields with good functional group tolerance in air. In addition, the quinazolinone derivatives were isolated from the reaction mixture of N-(2-(pyridin-2-yl)phenyl)benzamide with formamide or 5-nitroindole. The corresponding mechanism is discussed. These results indicate that 2-(pyridine-2-yl)aniline can serve as a directing group.

中文翻译:

发现2-(吡啶-2-基)苯胺作为乙酸铜介导的sp 2 C–H键胺化的导向基团

2-(吡啶-2-基)苯胺被设计为一个新的可移动的导向基团,用于促进由乙酸铜介导的C–H胺化。使用这种辅助剂,苯甲酰胺衍生物的β-C(sp 2)–H键可以用各种胺有效地胺化,产率中等至良好,并且在空气中具有良好的官能团耐受性。另外,从N-(2-(吡啶-2-基)苯基)苯甲酰胺与甲酰胺或5-硝基吲哚的反应混合物中分离出喹唑啉酮衍生物。讨论了相应的机制。这些结果表明2-(吡啶-2-基)苯胺可以用作指导基团。
更新日期:2017-08-09
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