本文選題：喹啉類化合物　切入點(diǎn)：Friedl(?)nder縮合反應(yīng)　出處：《東華理工大學(xué)》2017年碩士論文

【摘要】：作為一類非常重要的含氮雜環(huán)類化合物,喹啉類化合物憑借其重要的生物和藥理活性,在制藥、農(nóng)藥和染料等領(lǐng)域獲得了非常廣泛的應(yīng)用,也正因如此,其合成工作,特別是綠色合成法,近年來,已經(jīng)成為有機(jī)化學(xué)工作者們爭相研究的熱點(diǎn)。本論文利用Friedl(?)nder縮合反應(yīng),研究了三種合成喹啉類化合物的綠色新方法,主要研究內(nèi)容如下:(一)甲醇中α-糜蛋白酶催化合成喹啉類化合物:通過對(duì)酶源的篩選,確定出最佳催化劑為α-糜蛋白酶,并考察了反應(yīng)介質(zhì)、溫度和酶用量對(duì)反應(yīng)的影響,然后,在60℃條件下,以20 mgα-糜蛋白酶催化一系列2-氨基芳基酮和α-亞甲基酮之間的反應(yīng),合成了11種喹啉類化合物,獲得了40%~90%的產(chǎn)率。相比傳統(tǒng)催化劑,該法中的催化劑不僅催化活性高,而且具有良好的生物相溶性,在較溫和的反應(yīng)條件中展現(xiàn)出了良好的底物適用性。(二)離子液體水溶液中α-糜蛋白酶催化合成喹啉類化合物:考察了離子液體、離子液體含水量、反應(yīng)溫度以及酶用量對(duì)反應(yīng)的影響,然后,在55℃下,20%離子液體(1-乙基-3-甲基咪唑四氟硼酸鹽)水溶液中,以10 mgα-糜蛋白酶催化一系列2-氨基芳基酮和α-亞甲基酮,合成了14種喹啉類化合物,獲得了40%~94%的產(chǎn)率,與以有機(jī)溶劑為反應(yīng)介質(zhì)的體系相比,該體系條件更溫和、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機(jī)溶劑的使用。(三)深共熔溶劑中合成喹啉類化合物:考察了一些DES、溶劑、反應(yīng)溫度對(duì)反應(yīng)的影響,并在80℃,0.5 mL DES(氯化膽堿/草酸=1:1)中對(duì)一系列底物進(jìn)行了拓展,合成了11種喹啉類化合物,獲得了67%~94%的產(chǎn)率,相對(duì)于之前的研究,該法反應(yīng)時(shí)間更短、產(chǎn)率更高,同時(shí),DES可經(jīng)回收再利用,更符合綠色化學(xué)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.

【學(xué)位授予單位】：東華理工大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2017
【分類號(hào)】：O626.323

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本文編號(hào)：1656030