【摘要】：苯并咪唑化合物是一類重要的含氮雜環(huán)化合物,普遍存在于天然化合物與合成化合物中,是多種藥物的活性結(jié)構(gòu)單元。鑒于苯并咪唑化合物其獨特的結(jié)構(gòu)特性、反應(yīng)活性和生理活性等如此廣泛的應(yīng)用價值以及廣闊的市場前景,因此發(fā)展一種簡便,實用的苯并咪唑化合物的合成方法越來越受到科學(xué)家們的關(guān)注。在本論文中,我們首次闡述了一種簡便的銅鹽催化、疊氮化鈉參與的快速合成苯并咪唑化合物的方法。該方法具有良好的官能團(tuán)容忍性、反應(yīng)條件溫和、催化劑廉價易得等優(yōu)點。其中碘化亞銅引發(fā)SNAr反應(yīng)并輔助后續(xù)的單電子轉(zhuǎn)移氧化過程,以及促進(jìn)隨后的脫氮、環(huán)化過程,最終生成苯并咪唑化合物。1,2,4-三氮唑化合物也是一類重要的含氮雜環(huán)化合物,普遍存在于天然化合物與功能材料中。以1,2,4-三氮唑為核心的化合物,已經(jīng)在生物和藥物領(lǐng)域以及材料科學(xué)領(lǐng)域中得到了廣泛的應(yīng)用。同時1,3,5-三芳基取代-1,2,4-三氮唑化合物在太陽能電池、圖像傳感器、染料激光器和電致發(fā)光器件等領(lǐng)域中也有廣泛的應(yīng)用。因此,發(fā)展一種高效、簡便、溫和的制備方法備受科學(xué)家們的普遍關(guān)注。在本論文中,我們闡述了一種簡便、快速有效的以非金屬碘為催化劑,過氧化叔丁醇(70%水溶液)為氧化劑,以醛腙和脂肪胺為底物,發(fā)生自由基氧化偶聯(lián)反應(yīng),在空氣條件下即可高效合成一系列具有重要生物活性的1,3,5-三取代-1,2,4-三氮唑化合物的合成方法。該方法起始原料廉價易得,反應(yīng)條件溫和易控,反應(yīng)底物范圍廣泛,官能團(tuán)容忍性好并且可以輕易擴(kuò)大至克級,為合成1,3,5-三取代-1,2,4-三氮唑衍生物提供了一種簡便高效的方法。同時我們還應(yīng)用此方法合成了含有1,2,4-三氮唑結(jié)構(gòu)單元的芴類衍生物,并測定了其熒光性能。
[Abstract]:Benzimidazole compounds are a kind of important nitrogen-containing heterocyclic compounds, which are widely found in natural compounds and synthetic compounds, and are active structural units of many kinds of drugs. In view of the unique structural properties of benzimidazole compounds, their wide application value such as reaction activity and physiological activity, and their broad market prospects, they have developed a simple and convenient method for the development of benzimidazole compounds. The practical synthesis of benzimidazole compounds has attracted more and more attention of scientists. In this paper, we first described a simple method for the rapid synthesis of benzimidazole compounds catalyzed by copper salt and with the participation of sodium azide. The method has the advantages of good functional group tolerance, mild reaction conditions and cheap catalyst. Copper iodide initiated the SNAr reaction and assisted in the subsequent single electron transfer oxidation process, and promoted the subsequent denitrification and cyclization process to form benzimidazole compound. 4-triazole compounds are also an important class of nitrogen-containing heterocyclic compounds, which are widely found in natural compounds and functional materials. The compounds with the core of 1C 2N 4-triazole have been widely used in the fields of biology, medicine and material science. At the same time, 1C ~ (3) O _ (5) -triarylsubstituted -1H _ (2) O _ (4) -triazole compounds have been widely used in solar cells, image sensors, dye lasers and electroluminescent devices. Therefore, the development of an efficient, simple and mild preparation method has attracted widespread attention of scientists. In this paper, we described a simple, rapid and effective oxidative coupling reaction of tert butanol peroxide (70% aqueous solution) with nonmetallic iodine as catalyst, aldehyde-hydrazone and aliphatic amine as substrates. A series of important bioactive compounds of 1 ~ (3) O _ (5) -1 ~ (2 +) ~ (2) C _ (2) O _ (4-triazole) can be synthesized efficiently under air conditions. The initial raw material is cheap and easy to obtain, the reaction conditions are mild and easy to control, the reaction substrate is wide, the functional group tolerance is good and can be easily extended to gram class. 4-triazole derivatives provide a simple and efficient method. At the same time, we have synthesized fluorene derivatives containing 1 ~ (2) O ~ (4) -triazole structure unit by using this method, and have determined their fluorescence properties.
【學(xué)位授予單位】：浙江理工大學(xué)
【學(xué)位級別】：碩士
【學(xué)位授予年份】：2017
【分類號】：O626;O643.36

【參考文獻(xiàn)】

相關(guān)期刊論文 前1條

1 Rahul R.NAGAWADE;Devanand B.SHINDE;;BF_3·OEt_2 Promoted Solvent-free Synthesis of Benzimidazole Derivatives[J];Chinese Chemical Letters;2006年04期

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本文編號：2317452