铜催化氧化偶联合成多取代吡啶化合物

发布时间：2018-08-29 19:12

【摘要】：吡啶类化合物是一类公认的非常有价值的含氮六元杂环化合物,其在天然产物、药物和功能材料等领域都有着十分重要的地位。由于吡啶类化合物宝贵的应用价值,化学领域的科研工作者们一直在努力探索吡啶类化合物的合成方法及其应用价值,并取得了一系列丰硕的成果。尤其是过渡金属催化合成吡啶化合物的研究一直以来都是有机合成领域的一个热点,吸引着很多化学研究人员加入该研究行列。本文介绍了近几十年科研工作者们对合成吡啶类化合物方法的研究及其进展,另外详细介绍了我们实验小组研究的铜催化合成多取代吡啶化合物的新方法。论文主要由以下三个章节组成:第一章是对吡啶类化合物的应用价值以及合成方法研究的综述。我们主要介绍了近几十年来国内外研究人员报道的关于合成吡啶化合物的方法,并根据反应所用的催化剂种类的不同对合成方法进行了归纳阐述。第二章是基于以上介绍的研究成果,对我们课题组发展的铜催化氧化偶联合成多取代吡啶类化合物的新方法进行了详细介绍。新方法以肟酯衍生物为底物,将其与甲苯反应,反应以三氟甲基磺酸铜为催化剂,经氧化偶联反应,得到了一系列多取代吡啶化合物。该合成方法的特点是实现了sp3 C-H键的活化,具有成本低廉、反应条件温和、产率较高和底物适用性良好等优点。第三章是在此新方法的基础上,对多取代吡啶化合物的合成体系进行了拓展。我们引入苄胺和对甲苯磺酰腙作为结构单元,进一步开发出了新的多取代吡啶化合物的制备方法。
[Abstract]:Pyridine compounds are recognized as a class of highly valuable nitrogen-containing hexa-heterocyclic compounds, which play an important role in natural products, drugs and functional materials. Because of the valuable application value of pyridine compounds, researchers in the field of chemistry have been trying to explore the synthesis method and application value of pyridine compounds, and have achieved a series of fruitful results. Especially, the research on the synthesis of pyridine compounds catalyzed by transition metals has always been a hot topic in the field of organic synthesis, attracting many chemical researchers to join the research. In this paper, the research and progress in the synthesis of pyridine compounds by researchers in recent decades are introduced. In addition, a new method of copper-catalyzed synthesis of polysubstituted pyridine compounds studied by our experimental group is introduced in detail. The thesis consists of the following three chapters: the first chapter is a review of the application value of pyridine compounds and synthesis methods. We mainly introduced the methods of synthesis of pyridine compounds reported by domestic and foreign researchers in recent decades, and summarized the synthesis methods according to the different kinds of catalysts used in the reaction. In chapter 2, based on the above research results, a new method for the synthesis of polysubstituted pyridine compounds by copper catalytic oxidation coupling is introduced in detail. A series of polysubstituted pyridine compounds were synthesized by oxidative coupling reaction with toluene and copper trifluoromethyl sulfonate. The characteristic of this synthesis method is that the sp3 C-H bond is activated, which has the advantages of low cost, mild reaction conditions, high yield and good substrate applicability. In chapter 3, the synthesis system of polysubstituted pyridine compounds is extended based on the new method. Benzyl amines and p-toluenesulfonyl hydrazone were introduced as structural units to further develop a new method for the preparation of polysubstituted pyridine 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】：O626.32

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