三种绿色合成喹啉类化合物的方法研究

发布时间：2018-03-24 01:11

本文选题：喹啉类化合物　切入点：Friedl(?)nder缩合反应　出处：《东华理工大学》2017年硕士论文

【摘要】：作为一类非常重要的含氮杂环类化合物,喹啉类化合物凭借其重要的生物和药理活性,在制药、农药和染料等领域获得了非常广泛的应用,也正因如此,其合成工作,特别是绿色合成法,近年来,已经成为有机化学工作者们争相研究的热点。本论文利用Friedl(?)nder缩合反应,研究了三种合成喹啉类化合物的绿色新方法,主要研究内容如下:(一)甲醇中α-糜蛋白酶催化合成喹啉类化合物:通过对酶源的筛选,确定出最佳催化剂为α-糜蛋白酶,并考察了反应介质、温度和酶用量对反应的影响,然后,在60℃条件下,以20 mgα-糜蛋白酶催化一系列2-氨基芳基酮和α-亚甲基酮之间的反应,合成了11种喹啉类化合物,获得了40%~90%的产率。相比传统催化剂,该法中的催化剂不仅催化活性高,而且具有良好的生物相溶性,在较温和的反应条件中展现出了良好的底物适用性。(二)离子液体水溶液中α-糜蛋白酶催化合成喹啉类化合物:考察了离子液体、离子液体含水量、反应温度以及酶用量对反应的影响,然后,在55℃下,20%离子液体(1-乙基-3-甲基咪唑四氟硼酸盐)水溶液中,以10 mgα-糜蛋白酶催化一系列2-氨基芳基酮和α-亚甲基酮,合成了14种喹啉类化合物,获得了40%~94%的产率,与以有机溶剂为反应介质的体系相比,该体系条件更温和、所需酶量更少且催化效率更高,最重要的是避免了危害性有机溶剂的使用。(三)深共熔溶剂中合成喹啉类化合物:考察了一些DES、溶剂、反应温度对反应的影响,并在80℃,0.5 mL DES(氯化胆碱/草酸=1:1)中对一系列底物进行了拓展,合成了11种喹啉类化合物,获得了67%~94%的产率,相对于之前的研究,该法反应时间更短、产率更高,同时,DES可经回收再利用,更符合绿色化学的要求。
[Abstract]:As a very important class of heterocyclic compounds, quinoline compounds with important biological and pharmacological activity, pharmaceuticals, pesticides and dyes and other fields has been widely applied, because of this, the synthesis work, especially the green synthesis, in recent years, has become a hot topic in organic chemistry workers to research. This paper uses Friedl (?) nder condensation reaction, green three kinds of new methods for synthesis of quinoline compounds were studied, the main research contents are as follows: (a) alpha chymotrypsin catalyzed synthesis of quinoline compounds in methanol: through the screening of enzyme source, to determine the best catalyst for alpha chymotrypsin, and the effects of the reaction medium, temperature and amount of enzyme on the reaction and then, under the condition of 60 DEG C, with 20 mg of alpha chymotrypsin catalyzed by a series of 2- amino aryl ketone ketone and alpha methylene reaction, 11 quinoline synthesis Compounds, obtained the yield of 40%~90%. Compared with the traditional catalyst, the method of catalyst has high catalytic activity, but also has good biocompatibility, under mild reaction conditions show good applicability. The substrate (two) ionic liquid aqueous solution of alpha chymotrypsin catalyzed synthesis of quinoline compound: the effects of ionic liquids, ionic liquid water content, reaction temperature and enzyme dosage on the reaction, and then, at 55 DEG C, 20% ionic liquids (1- ethyl -3- methyl imidazole tetrafluoroborate) in aqueous solution with 10 mg of alpha chymotrypsin catalyzed by a series of 2- and alpha amino aryl ketone methylene ketones, 14 quinoline compounds were synthesized, obtained the yield of 40%~94%, compared with an organic solvent as a reaction medium of the system, the system of more moderate conditions, the enzymes required less and higher catalytic efficiency, the most important thing is to avoid the harm of organic solvents. The use of agents. (three) the synthesis of quinoline compounds in deep eutectic solvents: the effects of some DES, solvent, the effect of reaction temperature on the reaction, and at 80 degrees C, 0.5 mL DES (choline chloride / oxalic acid =1:1) in a series of substrate were developed, 11 kinds of quinoline compounds were synthesized and obtained the yield of 67%~94%, compared with the previous research, the shorter reaction time, higher yield, at the same time, DES can be recycled, more in line with the requirements of green chemistry.

【学位授予单位】：东华理工大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626.323

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