DABCO促进的对甲苯磺酰腙与硝基烯制备吡唑的方法

发布时间：2018-03-20 22:00

本文选题：合成　切入点：吡唑　出处：《兰州大学》2014年硕士论文　论文类型：学位论文

【摘要】：吡唑作为重要的有机杂环化合物因其结构的多样性和良好的生物活性近年来逐渐引起广大化学家的关注。大量研究和实践表明吡唑类化合物具有抗菌、抗痉挛、消炎、植物生长调节和抗血小板凝聚等生物活性。吡唑类化合物在农药领域作为植物保护性杀菌剂、除草剂、杀虫剂、除螨剂,在医药领域作为抗菌素、抗血栓药等方面有广泛的应用。我们发展了一种DABCO促进的由对甲苯磺酰腙和硝基烯制备多取代吡唑的方法。较之前报道的重氮化合物与缺电子烯烃或炔烃的1,3-偶极环加成反应,该反应没有经过重氮中间体,而以连续的Baylis-Hillman/分子内环化机制进行,并且反应的区域选择性得到了翻转,为多取代吡唑的合成提供了一条新颖、有效的途径。本论文主要分为三章。第一章综述了吡唑及其衍生物的应用,以及各种制备方法。第二章详细介绍了对甲苯磺酰腙与硝基烯在DABCO作用下合成吡唑类化合物的过程,同时对其反应机理进行了讨论。第三章实验部分是具体的实验方法以及波普数据。
[Abstract]:As an important organic heterocyclic compound, pyrazole has attracted the attention of chemists in recent years because of its diversity of structure and good biological activity. A large number of studies and practices have shown that pyrazole compounds have antibacterial, anti-spasmodic and anti-inflammatory properties. Pyrazole compounds are used as plant protective fungicides, herbicides, insecticides, mites, and antimicrobial agents in the field of medicine. Antithrombotic agents are widely used in many fields. We have developed a DABCO promoted method for the preparation of polysubstituted pyrazole from p-toluenesulfonyl hydrazone and nitrene. The diazo compounds have been reacted with 1 / 3 dipolar cycloaddition of electron-deficient olefins or alkynes without diazo intermediates. The intramolecular cyclization of Baylis-Hillman/ was carried out continuously, and the region selectivity of the reaction was reversed, which provided a novel and effective way for the synthesis of polysubstituted pyrazole. In chapter 1, the application of pyrazole and its derivatives and various preparation methods are reviewed. In chapter 2, the synthesis of pyrazole compounds with p-toluenesulfonyl hydrazone and nitroene under the action of DABCO is introduced in detail. At the same time, the reaction mechanism is discussed. In chapter 3, the experimental method and Pope data are discussed.
【学位授予单位】：兰州大学
【学位级别】：硕士
【学位授予年份】：2014
【分类号】：R914.5

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