本文選題：二三氟乙酸碘苯 + 四氫咔唑酮衍生物　； 參考：《天津大學(xué)》2014年碩士論文

【摘要】：四氫咔唑酮類(lèi)化合物，作為一類(lèi)重要的含氮雜環(huán)化合物，近年來(lái)在醫(yī)藥化工領(lǐng)域被發(fā)現(xiàn)在諸多方面具有突出的生物活性，包括抗菌、抗艾滋病病毒、抗人類(lèi)乳頭狀瘤病毒、抗朊病毒、抗癌等。正因如此，越來(lái)越多的研究人員將精力投入到對(duì)此類(lèi)化合物的合成研究中來(lái)，迄今已經(jīng)開(kāi)發(fā)出了多種合成路線和方法。本論文基于課題組之前在高價(jià)碘化物介導(dǎo)下碳碳鍵偶聯(lián)制備吲哚類(lèi)衍生物相關(guān)的研究成果，提出在二三氟乙酸碘苯（PIFA）作用下，，通過(guò)非金屬條件下碳碳鍵氧化偶聯(lián)的方式構(gòu)建碳碳鍵，從而實(shí)現(xiàn)對(duì)該類(lèi)化合物的分子內(nèi)環(huán)合構(gòu)建。 本論文以環(huán)己酮、環(huán)庚酮、以及含有各種取代基的苯胺為最初始原料，通過(guò)已有文獻(xiàn)方法，制備了一系列的2-取代氨基環(huán)己基-2-烯酮類(lèi)化合物和2-取代氨基環(huán)庚基-2-烯酮類(lèi)化合物作為底物。這兩類(lèi)底物，在二三氟乙酸碘苯（PIFA）的氧化作用下，分別以乙酸酐（Ac2O）和三氟乙醇（TFE）作為溶劑，順利生成了相應(yīng)的環(huán)合產(chǎn)物，反應(yīng)效率高，操作簡(jiǎn)單易行，方便快捷。在此條件下，我們構(gòu)建了一系列的四氫咔唑酮類(lèi)產(chǎn)物及其衍生物，并在研究此方法學(xué)應(yīng)用范圍與限度之后，進(jìn)一步研究了此反應(yīng)的反應(yīng)機(jī)制，提出了我們的設(shè)想，并做了相關(guān)驗(yàn)證。 本文用上述方法得一系列四氫咔唑酮類(lèi)化合物及其衍生物，產(chǎn)物的結(jié)構(gòu)均得到高分辨質(zhì)譜、核磁共振氫譜、核磁共振碳譜等表征數(shù)據(jù)的佐證。
[Abstract]:Tetrahydrocarbazolones, as an important class of nitrogen-containing heterocyclic compounds, have been found in recent years in the field of medicine and chemical industry with outstanding biological activities, including antibacterial, anti-HIV, anti-human papillomavirus. Anti-prion, anticancer, etc. As a result, more and more researchers have devoted their efforts to the synthesis of these compounds, and many synthetic routes and methods have been developed. Based on the previous studies on the preparation of indole derivatives by carbon-carbon bond coupling under the guidance of high valence iodides, this paper proposes a novel method for the preparation of indole derivatives under the action of PIFA (difluoroacetic acid). Carbon bonds were constructed by oxidative coupling of carbon and carbon bonds under nonmetallic conditions, thus the intramolecular cyclization of these compounds was realized. In this paper, cyclohexanone, cycloheptanone and aniline containing various substituents were used as the initial raw materials. A series of 2-substituted amino cyclohexyl-2-enones and 2-substituted amino cycloheptyl-2-enones were prepared as substrates. These two kinds of substrates were oxidized by difluoroacetic acid iodibenzylidene (PIFA) with acetic anhydride (Ac2OO) and trifluoroethanol (TFEE) as solvents respectively. The corresponding cyclization products were produced successfully. The reaction efficiency was high, the operation was simple and convenient. Under these conditions, we have constructed a series of tetrahydrocarbazolones and their derivatives. After studying the scope and limits of the methodology, we have further studied the reaction mechanism and put forward our ideas. And the relevant verification is done. In this paper, a series of tetrahydrocarbazolones and their derivatives were obtained by using the above method. The structures of the products were confirmed by the characterization data of high resolution mass spectrometry, nuclear magnetic resonance (NMR) and nuclear magnetic resonance (NMR) carbon spectroscopy.
【學(xué)位授予單位】：天津大學(xué)
【學(xué)位級(jí)別】：碩士
【學(xué)位授予年份】：2014
【分類(lèi)號(hào)】：R914.5

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