炔烃偶联及喹啉衍生物卤化反应研究

发布时间：2018-03-23 23:10

本文选题：炔酸　切入点：末端炔　出处：《温州大学》2017年硕士论文

【摘要】：在有机合成化学中,通常通过偶联反应构建碳-碳键,碳-杂键,从而将简单的小分子转变为结构复杂、功能多样的分子。同时,炔烃是有机合成化学中的重要结构单元或通用中间体,存在于众多具备生物活性的分子和功能材料中。因此,炔烃的偶联反应得到了广泛的研究。卤代喹啉类化合物存在于众多具有生物和药理活性的天然产物以及市售药物中,值得我们寻找更加简便、高效的方法来合成该类化合物。本论文围绕炔烃偶联和喹啉衍生物卤化反应展开论述,分为以下四部分:(1)简单综述了近年来炔酸脱羧偶联反应和末端炔烃脱氢偶联反应的研究进展;(2)发展了钯催化下利用易储存的炔酸与烯丙基醚脱羧偶联反应合成共轭1,3-烯炔化合物。该反应条件温和,副产物绿色环保;(3)探索研究了镍催化末端炔烃与C(sp~2)-H偶联得到炔基化/环化产物,利用N,S双齿导向基团合成3-亚甲基异吲哚啉酮化合物;(4)探索研究了喹啉衍生物卤化反应,发展了一种非金属催化的喹啉衍生物C5位选择性卤化方法。该反应操作简便、绿色环保、产物易得。
[Abstract]:In organic synthesis chemistry, carbon-carbon bonds, carbon-hetero-bonds are usually formed by coupling reactions, thus transforming simple small molecules into complex structurally diverse molecules. Alkynes are important structural units or universal intermediates in organic synthesis chemistry, which are found in many bioactive molecular and functional materials. The coupling reaction of alkynes has been extensively studied. Halogenated quinoline compounds are found in many natural products with biological and pharmacological activities as well as marketable drugs. This paper focuses on the coupling of alkynes and halogenation of quinoline derivatives. In this paper, the research progress of decarboxylation of alkynic acid and dehydrogenation of terminal alkynes is briefly reviewed. The palladium catalyzed synthesis of allyl ether and alkylidene by palladium catalyzed decarboxylation of alkynic acid with allyl ether is reviewed. The reaction conditions are mild. The byproduct was green and environmental friendly. The alkynylation / cyclization product was synthesized by coupling terminal alkynes with C(sp~2)-H catalyzed by nickel, and 3-methyleneisoindolinone compound was synthesized by N (S) didentate guide group. The halogenation reaction of quinoline derivatives was studied, and the halogenation of quinoline derivatives was studied. A nonmetal-catalyzed selective halogenation method for quinoline derivatives at C _ 5 site was developed. The reaction is simple, environmentally friendly and the products are easy to obtain.
【学位授予单位】：温州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O621.25

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