系列含氮化合物的合成

发布时间：2018-05-09 15:40

本文选题：氮杂环 + 苯并咪唑　；参考：《郑州大学》2017年硕士论文

【摘要】：许多氮杂环化合物具有生理和药物活性,其中苯并咪唑类、喹喔啉类、吲哚及其衍生物更是在医药、农药及染料等领域被广泛应用,因此研究氮杂环化合物的合成具有重要的意义。通过胺类与醛缩合反应制备氮杂环是有机合成中主要反应类型之一。本论文选取了几种合成方法,对苯并吡嗪类、苯并咪唑类和吲哚类化合物的合成方法进行了研究,通过环化缩合制备了目标产物,利用核磁共振氢谱对其结构进行了验证。论文首先简要概述了含氮杂环化合物的应用研究进展,对苯并咪唑类、喹喔啉类、吲哚及其衍生物的不同合成途径的优缺点进行了总结。研究了以取代邻苯二胺类化合物为起始原料,分别与乙酰丙酮和冰乙酸发生缩合反应制备苯并咪唑类化合物的方法,并对两种反应方法进行了优化比较。采用邻苯二胺类与乙酸反应制备苯并咪唑类化合物的方法,反应物比例采用摩尔量之比邻苯二胺:乙酸=1:2,催化剂多聚磷酸质量为反应底物质量的10倍,反应时间为2～4 h,“一锅法”实现了苯并咪唑类的合成。此反应过程绿色、温和、原料易得、操作简单,有利于工业化生产。通过对苯并吡嗪类化合物的不同合成方法进行比较,以邻苯二胺与乙二醛为原料制备了苯并咪唑类化合物。该法不仅环保省时,而且操作简单。采用摩尔量之比邻苯二胺:乙酸=1:1.5,反应时间一般为4 h,以水为溶剂,经环化缩合制得目标化合物,反应总收率达到65 %以上。本论文还研究了吲哚与各取代芳香醛反应制备二甲基吲哚类化合物的反应。以单质碘为催化剂,乙腈为溶剂,室温条件下即可得到目标产物,总收率达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%.
【学位授予单位】：郑州大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626

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