“一锅法”合成5-芳基-1H-吡唑衍生物及其生物活性研究

发布时间：2018-05-18 06:55

本文选题：一锅法 + 吡唑衍生物　；参考：《湖北工业大学》2017年硕士论文

【摘要】：吡唑类化合物具有良好的生物活性,被广泛的应用于农药和医药领域。因此,合成具有多样性取代基的吡唑类化合物,对农药和医药的创制有非常重大意义。为了探索具有较好的生物活性的吡唑类农药,本文总结了吡唑类化合物在农药和医药领域中的应用进展和目前比较成熟的合成工艺方法。近些年发展起来的“一锅合成法”逐渐成为热门的绿色简便的新型有机合成方法,具有操作简便,产率高等特点。本论文将“一锅分步加料”法与传统的吡唑合成方法相结合,首先用强碱将含α-H的酮转化为烯醇化中间体,再加入酰氯与之反应生成1,3-二羰基化合物中间体,最后加入水合肼与1,3-二羰基化合物发生环缩合反应合成一系列5-芳基-1H吡唑衍生物。实验中,探索了每一步反应条件,包括溶剂类型、碱及其用量、反应温度、反应时间、反应底物摩尔配比等,并对反应条件进行优化,同时对反应底物进行拓展,最终获得了一系列吡唑衍生物。所合成的18个新型吡唑化合物都经过了IR,1H NMR,GC-MS进行结构表征,并且对波谱数据都进行了分析,部分化合物还通过单晶衍射对晶体结构进行了表征。论文对合成的18个5-芳基-1H-吡唑化合物进行了杀虫、除草和杀菌活性的测试。实验结果表明,吡唑环5-位芳基上含有甲氧基的化合物5c~5j、5n-5o对浮萍、小白菜和狗芽根表现出一定的抑制活性,化合物5c~5e、5g~5h、5j、5n~5o表现出一定的杀菌活性。化合物5h对单子叶禾木科杂草狗芽根的抑制率达66.6%,同时5h对小麦赤霉菌的抑制活性达到51.9%,具有深入研究价值和应用前景。
[Abstract]:Pyrazole compounds have good biological activity and are widely used in pesticide and medicine fields. Therefore, the synthesis of pyrazole compounds with various substituents is of great significance to the creation of pesticides and medicines. In order to explore pyrazole pesticides with good biological activity, the application of pyrazole compounds in the field of pesticides and medicine and the mature synthetic methods are summarized in this paper. The "one pot synthesis method" developed in recent years has gradually become a popular green and simple new organic synthesis method with the characteristics of simple operation and high yield. In this paper, the "one-pot step feeding" method was combined with the traditional method of pyrazole synthesis. Firstly, 伪 -H containing ketones were converted into enalcoholated intermediates with strong base, and then acyl chloride was added to the intermediates to form 1o 3-dicarbonyl compounds. Finally, a series of 5-aryl -1H pyrazole derivatives were synthesized by cyclic condensation of hydrazine hydrate with 1 ~ (3) -dicarbonyl compound. In the experiment, the reaction conditions, including solvent type, alkali and its dosage, reaction temperature, reaction time, molar ratio of substrate and so on, were explored, and the reaction conditions were optimized and the reaction substrate was expanded. Finally, a series of pyrazole derivatives were obtained. All of the 18 new pyrazole compounds were characterized by IR 1H NMR-GC-MS and the spectral data were analyzed. Some of the compounds were characterized by single crystal diffraction. The insecticidal, herbicidal and fungicidal activities of 18 5-aryl-1 H-pyrazole compounds were tested. The results showed that the compounds containing methoxy group on the 5-position of pyrazole ring showed certain inhibitory activity on duckweed, pakchoi and dog bud roots, and the compounds 5c5e5e5e5g ~ 5h ~ (5) J ~ (5) J ~ (5) N ~ (5) o showed certain fungicidal activity to the duckweed, pakchoi and dog bud roots. The inhibition rate of the compound on the root of the dog bud of the monocotyledonous grasses reached 66.6 for 5 h, while the inhibitory activity against gibberelly reached 51.9 for 5 h. It has the value of further study and the prospect of application.
【学位授予单位】：湖北工业大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626

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