串联叠氮化环化反应合成含氮杂环化合物的方法学研究

发布时间：2018-08-22 09:13

【摘要】：叠氮化合物是一类重要的有机化合物,也是合成其它含氮化合物的常用中间体。本文主要论述了有机叠氮化合物的自由基反应用于构建C-N键的合成策略,主要包括三部分的内容。第一章里,从以下两方面对近年来的有机叠氮化合物参与的C-N成键反应做了简要的文献综述:(1)利用自由基反应制备有机叠氮化合物;(2)通过有机叠氮化合物的自由基反应构建C-N键。第二章和第三章为硕士期间的研究工作,概括如下:(1)利用N-芳基烯胺的叠氮化/环化反应,发展了新的合成喹喔啉的方法学。该方法采用N-亚芳基胺和TMSN3作为起始原料,碘苯二乙酸作为氧化剂,以串联的形式实现了两次C-N键的氧化偶联。该方法条件简便温和,合成效率高,具有一定的实际应用价值。(2)在上述工作基础上,以烯胺和TMSN3作为初始原料,碘苯二乙酸/醋酸铜/四丁基碘化铵为催化氧化体系,实现了C(sp2)-H和C(sp3)-H的串联双胺化。该反应为合成三氟甲基取代的咪唑类化合物提供了新的方法学。
[Abstract]:Azide compounds are important organic compounds and intermediates in the synthesis of other nitrogenous compounds. In this paper, the synthesis strategy of the free radical reaction of organic azide compounds for the construction of C-N bond is discussed, which includes three parts. In the first chapter, A brief review of the C-N bonding reactions involving organic azide compounds in recent years has been made in the following two aspects: (1) the synthesis of organic azide compounds by free radical reaction; (2) the formation of C-N bonds by free radical reaction of organic azide compounds. The second and third chapters are the research work during the master period, which are summarized as follows: (1) A new methodology for the synthesis of quinoxaline has been developed by using the azide / cyclization reaction of N-arylenamine. In this method, N-aryl amines and TMSN3 were used as starting materials and iodobenzenediacetic acid as oxidant to realize the oxidative coupling of C-N bond in series. The method is simple and mild, and has high synthesis efficiency. (2) on the basis of the above work, enamine and TMSN3 were used as initial raw materials, and iodophenodiacetic acid / copper acetate / tetramethylammonium iodide was used as catalytic oxidation system. The series diamination of C (sp2) -H and C (sp3) -H was realized. This reaction provides a new methodology for the synthesis of trifluoromethyl substituted imidazole compounds.
【学位授予单位】：兰州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626

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