基于C-H活化的（异）吲哚酮合成方法的研究

发布时间：2018-11-12 12:49

【摘要】：吲哚酮/异吲哚酮类化合物及其衍生物是一类重要的含氮杂环化合物,其广泛存在于天然化合物和药物骨架中。由于其独特的生物活性以及潜在的巨大应用价值,此类化合物得到了有机化学家们的关注。近年来,吲哚酮/异吲哚酮类化合物的合成方法呈现出越来越多样化。发展简单高效的方法合成吲哚酮和异吲哚酮及其衍生物具有重要的研究价值和实际意义,符合绿色化学的发展理念。本论文主要围绕吲哚酮和异吲哚酮类化合物的合成方法展开研究,具体工作如下:(1)室温条件下可见光促进铁催化的N-芳基丙烯酰胺和二甲基亚砜(DMSO)甲基化环化合成吲哚酮的反应。在这部分工作中,我们通过自由基串联过程,在3W白光LED光源促进和铁催化的N-芳基丙烯酰胺双官能化来实现制备各种3-乙基-3-甲基吲哚酮的方法。该方法条件简单温和,不需外加光敏化剂,为合成吲哚酮类化合物提供了新方法。(2)钯催化的新N,O-双齿导向基团和丙烯酸酯合成多取代异吲哚啉酮类化合物。该反应以N-邻乙酰基苯基苯甲酰胺和丙烯酸酯为原料,通过醋酸钯活化邻位C H键并进一步环化合成异吲哚酮类化合物,具有条件相对温和、较好的官能团容忍性以及良好区域选择性的特点,为合成多取代异吲哚酮提供了新的方法。
[Abstract]:Indole / isoindole compounds and their derivatives are a kind of important nitrogen-containing heterocyclic compounds, which are widely found in natural compounds and drug skeletons. Due to their unique biological activity and potential great application value, these compounds have attracted the attention of organic chemists. In recent years, the synthesis methods of indole / isoindole compounds have become more and more diversified. The development of a simple and efficient method for the synthesis of indole ketone, isoindole ketone and its derivatives has important research value and practical significance, and accords with the development concept of green chemistry. This thesis focuses on the synthesis of indole ketones and isoindole ketones. The main works are as follows: (1) visible light at room temperature can promote the cyclization of N-aryl acrylamide and dimethyl sulfoxide (DMSO) to indole ketone catalyzed by iron. In this part of the work, we have prepared various kinds of 3-ethyl-3-methylindole ketones by free radical series process in 3W white light LED light source and iron-catalyzed difunctionalization of N-aryl acrylamide. The conditions of this method are simple and mild, and the addition of Guang Min is not needed, which provides a new method for the synthesis of indole ketones. (2) Palladium catalyzed synthesis of polysubstituted iso-indolinone ketones by palladium catalyzed new NCO-didentate group and acrylate. In this reaction, N-o-acetylbenzoamide and acrylate were used as raw materials to activate the O-C-H bond by palladium acetate and to further cyclize the iso-indole ketones. The conditions were relatively mild. Better functional tolerance and good regioselectivity provide a new method for the synthesis of polysubstituted isoindole ketones.
【学位授予单位】：淮北师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626

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