本文選題：氮雜環(huán) + 苯并咪唑�。� 參考：《鄭州大學》2017年碩士論文

【摘要】：許多氮雜環(huán)化合物具有生理和藥物活性,其中苯并咪唑類、喹喔啉類、吲哚及其衍生物更是在醫(yī)藥、農(nóng)藥及染料等領(lǐng)域被廣泛應(yīng)用,因此研究氮雜環(huán)化合物的合成具有重要的意義。通過胺類與醛縮合反應(yīng)制備氮雜環(huán)是有機合成中主要反應(yīng)類型之一。本論文選取了幾種合成方法,對苯并吡嗪類、苯并咪唑類和吲哚類化合物的合成方法進行了研究,通過環(huán)化縮合制備了目標產(chǎn)物,利用核磁共振氫譜對其結(jié)構(gòu)進行了驗證。論文首先簡要概述了含氮雜環(huán)化合物的應(yīng)用研究進展,對苯并咪唑類、喹喔啉類、吲哚及其衍生物的不同合成途徑的優(yōu)缺點進行了總結(jié)。研究了以取代鄰苯二胺類化合物為起始原料,分別與乙酰丙酮和冰乙酸發(fā)生縮合反應(yīng)制備苯并咪唑類化合物的方法,并對兩種反應(yīng)方法進行了優(yōu)化比較。采用鄰苯二胺類與乙酸反應(yīng)制備苯并咪唑類化合物的方法,反應(yīng)物比例采用摩爾量之比鄰苯二胺:乙酸=1:2,催化劑多聚磷酸質(zhì)量為反應(yīng)底物質(zhì)量的10倍,反應(yīng)時間為2～4 h,“一鍋法”實現(xiàn)了苯并咪唑類的合成。此反應(yīng)過程綠色、溫和、原料易得、操作簡單,有利于工業(yè)化生產(chǎn)。通過對苯并吡嗪類化合物的不同合成方法進行比較,以鄰苯二胺與乙二醛為原料制備了苯并咪唑類化合物。該法不僅環(huán)保省時,而且操作簡單。采用摩爾量之比鄰苯二胺:乙酸=1:1.5,反應(yīng)時間一般為4 h,以水為溶劑,經(jīng)環(huán)化縮合制得目標化合物,反應(yīng)總收率達到65 %以上。本論文還研究了吲哚與各取代芳香醛反應(yīng)制備二甲基吲哚類化合物的反應(yīng)。以單質(zhì)碘為催化劑,乙腈為溶劑,室溫條件下即可得到目標產(chǎn)物,總收率達69 %左右。
[Abstract]:Many nitrogen heterocyclic compounds have physiological and drug activities, among which benzimidazole, quinoxaline, indole and their derivatives are widely used in medicine, pesticides and dyes. Therefore, it is of great significance to study the synthesis of nitrogen heterocyclic compounds. The synthesis of nitrogen heterocycles by condensation of amines with aldehydes is one of the main reactions in organic synthesis. In this paper, several synthetic methods were selected to study the synthesis of benzopyrazines, benzimidazoles and indole compounds. The target products were prepared by cyclization condensation, and their structures were verified by nuclear magnetic resonance spectroscopy (NMR). In this paper, the research progress of nitrogen-containing heterocyclic compounds is briefly reviewed, and the advantages and disadvantages of benzimidazole, quinoxaline, indole and their derivatives are summarized. The synthesis of benzimidazole compounds by condensation of acetylacetone and glacial acetic acid with substituted o-phenylenediamine compounds as starting materials was studied. Benzimidazole compounds were prepared by the reaction of o-phenylenediamine with acetic acid. The molar ratio of o-benzenediamine to acetic acid was 1: 2, and the mass of polyphosphoric acid of catalyst was 10 times of that of the substrate. Benzimidazole was synthesized by one-pot method in the reaction time of 2g / 4h. The reaction process is green, mild, easy to obtain raw materials, easy to operate, conducive to industrial production. Benzimidazole compounds were prepared from o-phenylenediamine and Glyoxal by comparing different synthetic methods of benzopyrazines. The method is not only environmentally friendly and time saving, but also simple to operate. The target compound was synthesized by cyclization and condensation with molar ratio of o-phenylenediamine to acetic acid 1: 1.5, reaction time 4 h, water as solvent and cyclization. The total yield of the reaction was over 65%. The reaction of indole with substituted aromatic aldehydes to prepare dimethyl indole compounds was also studied. Using iodine as catalyst and acetonitrile as solvent, the target product can be obtained at room temperature. The total yield is about 69%.
【學位授予單位】：鄭州大學
【學位級別】：碩士
【學位授予年份】：2017
【分類號】：O626

【參考文獻】

相關(guān)期刊論文 前9條

1 喻小龍;聶仁峰;魯新環(huán);周丹;夏清華;;氮雜活性炭負載鈀的制備及其在苯甲酸水相加氫中的應(yīng)用[J];湖北大學學報(自然科學版);2017年01期

2 賀云;范桂娟;張光全;黃明;劉玉存;;5-氨基-3-硝基-1,2,4-三唑的合成及反應(yīng)性研究進展[J];含能材料;2012年06期

3 邢燁;解正峰;劉方明;;磷鎢酸催化合成雙吲哚甲烷衍生物[J];應(yīng)用化學;2009年03期

4 呂延文;2,3-二氯喹喔啉-6-羧酰氯的合成新工藝[J];染料與染色;2004年04期

5 Sakina Hayat BENABADJI;Anticarcinogenic and antioxidant activity of diindolylmethane derivatives[J];Acta Pharmacologica Sinica;2004年05期

6 孫建平,吳洪才,李寶銘,應(yīng)祖金;側(cè)鏈含偶氮非線性光學活性基團的聚酰亞胺的合成與表征[J];西安交通大學學報;2003年06期

7 曹玉娟,高海翔,魯潤華;胍類催化劑[J];化學通報;2003年04期

8 李謙和,尹篤林,伏再輝;2,3-二甲基吡嗪合成工藝的改進[J];合成化學;1997年02期

9 闕浩泉,徐芳,陳克潛;2—苯基—3—嗎啉基喹喔啉的合成[J];蘇州大學學報(自然科學);1994年04期

相關(guān)碩士學位論文 前1條

1 王玉;幾種氮雜環(huán)化合物的合成研究[D];南京理工大學;2012年

，

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