氮杂环卡宾催化实现的含氮杂环类化合物的功能化研究

发布时间：2018-05-28 04:37

本文选题：含氮杂环化合物 + 氮杂环卡宾　；参考：《贵州大学》2017年硕士论文

【摘要】：含氮杂环化合物作为有机合成领域的重要合成单元,常见于天然产物、材料、医药及农药分子骨架中,由于其独特的生物活性引起了有机合成领域的高度重视,如何利用高效、简洁的合成策略构建含氮杂环类化合物一直是本领域域的研究热点和难点。吲哚类化合物是含氮杂环化合物中的重要一员,其高效的生物活性已被深入研究并得到了广泛的应用。如何实现含吲哚类骨架化合物的精修并合成出结构新颖的吲哚类衍生物一直是有机合成领域的热点。有机小分子催化剂是近年来有机催化领域的研究重点之一,氮杂环卡宾作为有机小分子催化剂中的后起之秀由于其独特的催化活化模式受到了科研人员的深入研究并得到了迅速发展。羰基类化合物的?-位活化是氮杂化卡宾催化领域的重要活化模式之一。因此本论文主要研究了氮杂环卡宾催化吲哚芳杂醛的支链γ-位sp3碳原子的活化,构建结构新颖的吲哚衍生物及其生物活性研究等两个方面的内容。1.在氮杂环卡宾催化剂和联苯二醌氧化剂的作用下,催化氧化3-甲基-2-吲哚醛的sp3碳原子活化,形成环外双烯醇式中间体与三氟苯乙酮反应,以氧杂Diels-Alder环加成方式反应,在室温条下,以高的收率一步构建含有六元环内酯、季碳中心、三氟甲基以吲哚为主要骨架的螺环化合物。此方法以高效简洁的方式,实现吲哚类化合物的多官能团化,合成出结构新颖的吲哚衍生物,并成功实现了吲哚这类芳杂醛环外碳原子的活化,为芳醛γ-位碳原子的活化提供理论依据。2.通过使用浊度法,对已合成出的部分目标化合物,进行生物活性测试,发现化合物3p在浓度为200和100μg/m L时对水稻白叶枯细菌的抑制率均为100%,其他化合物对这两种植物细菌抑菌活性较差。
[Abstract]:As an important synthetic unit in the field of organic synthesis, nitrogen-containing heterocyclic compounds are commonly used in natural products, materials, medicine and pesticide molecular skeletons. Because of their unique biological activities, they have attracted great attention in the field of organic synthesis. The construction of heterocyclic compounds containing nitrogen by simple synthesis strategy has been a hotspot and difficulty in this field. Indole compounds are important members of nitrogen-containing heterocyclic compounds, and their highly effective biological activities have been deeply studied and widely used. How to refine the indole skeleton compounds and synthesize novel indole derivatives has been a hotspot in the field of organic synthesis. In recent years, small organic catalyst is one of the most important research fields in the field of organic catalysis. Nitrogen heterocyclic carbene as a rising star of organic small molecule catalysts has been deeply studied and developed rapidly because of its unique catalytic activation mode. The activation of carbonyl compounds is one of the most important activation modes in the field of nitrogen hybrid carbene catalysis. In this thesis, the activation of 纬-sp3 carbon atom in the branched chain of indole aromatic aldehyde catalyzed by carbene was studied, and two novel indole-derived derivatives were constructed and their biological activities were studied. The sp3 carbon atom of 3-methyl-2-indolaldehyde was activated by the catalytic oxidation of 3-methyl-2-indolaldehyde under the action of aza-heterocyclic carbene catalyst and biquinone oxidant, which formed an extracyclic dienol intermediate reacting with trifluoroacetophenone. The reaction was carried out in the form of oxygen-heterocyclic Diels-Alder cycloaddition. At room temperature, the spirocyclic compounds containing hexachlorolactone, quaternary carbon center and indole-like backbone of trifluoromethyl were synthesized in one step with high yield. In this method, the multi-functional group of indole compounds was realized, and the novel indole derivatives were synthesized, and the activation of carbon atoms outside the ring of aromatic aldehydes such as indole was successfully realized. It provides a theoretical basis for the activation of aromatic aldehydes 纬 -site carbon atom. By using the turbidimetric method, the bioactivity of some of the target compounds has been tested. It was found that the inhibition rate of compound 3p to rice white leaf blight bacteria was 100 at the concentrations of 200 and 100 渭 g / mL, while the other compounds had poor antibacterial activity against these two plant bacteria.
【学位授予单位】：贵州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626

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