本文選題：2　切入點(diǎn)：4　出處：《蘭州大學(xué)》2017年碩士論文

【摘要】：吡啶和喹喔啉是兩類非常重要的含氮雜環(huán)化合物。本文詳細(xì)介紹了近幾十年來吡啶類化合物的應(yīng)用及其合成方法的研究進(jìn)展,銅催化合成多取代吡啶的新方法以及合成喹喔啉類化合物的新方法。主要由以下三部分組成:第一部分,主要是對(duì)吡啶類化合物的應(yīng)用及其合成進(jìn)展的綜合概述。首先,吡啶類化合物因吡啶環(huán)結(jié)構(gòu)的存在而具有的生物和醫(yī)藥活性,使其在生物化學(xué)、藥物化學(xué)、農(nóng)藥化學(xué)、有機(jī)合成化學(xué)、功能材料、染料等諸多領(lǐng)域有著廣泛的應(yīng)用。其次,根據(jù)合成吡啶類化合物有無金屬催化以及金屬催化下的合成類型進(jìn)行分類,并對(duì)其合成方法進(jìn)行綜述。我們發(fā)現(xiàn),非金屬催化合成吡啶的方法具有經(jīng)濟(jì)、環(huán)保、低毒等優(yōu)點(diǎn),因而有著很好的發(fā)展前景。然而,大部分吡啶合成方法需要金屬催化劑的加入,我們主要對(duì)金屬催化下環(huán)異構(gòu)法、[4+2]環(huán)加成、[3+3]環(huán)加成、[3+2+1]環(huán)加成、[2+2+2]環(huán)加成、[2+2+1+1]環(huán)加成法等六大類的吡啶合成方法進(jìn)行了綜述。第二部分,2,4,6-三取代吡啶類化合物的合成。多取代吡啶是一種廣泛存在于天然產(chǎn)物、醫(yī)藥、功能材料和農(nóng)業(yè)化學(xué)等領(lǐng)域的結(jié)構(gòu)骨架。該部分介紹了一種合成多取代吡啶類化合物的新方法,即銅催化氧化條件下,肟酯類化合物與N-苯甘氨酸酯類化合物發(fā)生[3+2+1]環(huán)加成反應(yīng),快速有效的合成2,4,6-三取代吡啶類化合物。該方法有著良好的官能團(tuán)兼容性,同時(shí)產(chǎn)物上酯基的保留為進(jìn)一步合成吡啶衍生物提供了可能。特別的,該方法為合成2,6-對(duì)稱取代異煙酸酯這類多取代吡啶提供了一條新穎的合成路線。第三部分,喹喔啉類化合物的合成。該部分介紹了一種合成喹喔啉類化合物的新方法,即以碘化亞銅為催化劑,L-脯氨酸為配體,在堿性條件下,鄰碘苯胺、疊氮鈉和1-苯基-2-(苯基氨基)乙酮通過三組分一鍋法成功合成了喹喔啉類化合物。在該方法中,疊氮鈉作為氮源成功地為目標(biāo)產(chǎn)物提供了一個(gè)氮原子,從而解決了傳統(tǒng)方法中以鄰苯二胺為底物時(shí)容易生成同分異構(gòu)體這一難題。
[Abstract]:Pyridine and quinoxaline are two kinds of important nitrogenous heterocyclic compounds. This paper describes the research progress in recent years application of pyridine compounds and synthetic methods, a new method of copper catalyzed synthesis of substituted pyridine and a new method of synthesis of quinoxaline compounds. The main consists of three parts: the first part mainly. Is a comprehensive overview of application of pyridine compounds and their synthesis. Firstly, pyridine compounds due to the presence of pyridine ring structure with biological and medicinal activities, the biochemistry, pharmaceutical chemistry, pesticide chemistry, organic synthesis, functional materials, dyes and other fields are widely used. Secondly, according to the synthesis of pyridine compounds with metal catalysis and synthesis of type metal catalyzed to classify and summarize the synthesis method. We found that non metal catalyzed synthesis Pyridine method has the advantages of economy, environmental protection, low toxicity, and has a very good development prospects. However, adding most pyridine synthesis methods need metal catalyst, we focused on the metal catalyzed heterogeneous ring method, [4+2] cycloaddition, [3+3] cycloaddition, [3+2+1] cycloaddition, [2+2+2] cycloaddition, pyridine methods for the synthesis of six kinds of [2+2+1+1] ring plus method were reviewed. The second part, the synthesis of 2,4,6- three substituted pyridine compounds. Multi substituted pyridine is widely present in natural products, pharmaceuticals, agricultural chemical and functional materials such as the structure of the skeleton. This part introduces a new method of substituted pyridine many compounds, namely copper catalyzed oxidation conditions, oxime esters and N- phenylglycine ester compounds [3+2+1] cycloaddition reaction, synthesis of fast and effective 2,4,6- three substituted pyridine compounds. This method has a good Functional compatibility, while retaining the ester product provides the possibility for further synthesis of pyridine derivatives. In particular, the method for the synthesis of 2,6- substituted isonicotinic acid ester of this kind of symmetrical polysubstituted pyridine provides a novel synthetic route. The third part, the synthesis of quinoxaline compounds. This part introduces a new method the synthesis of quinoxaline compounds, namely cuprous iodide as catalyst, L- as ligand of proline, under alkaline conditions, o-iodine aniline, sodium azide and 1- phenyl -2- (phenylamino) ethanone synthesis of quinoxaline compounds through the three component one pot method. In this method, sodium azide as nitrogen the source of success for the target product provides a nitrogen atom, so as to solve the traditional method in the adjacent benzene two amine is easy to generate the problem of isomeric substrate.

【學(xué)位授予單位】：蘭州大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2017
【分類號(hào)】：O626

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