可见光促进的吲哚环的构建及其官能化反应

发布时间：2018-04-18 04:04

本文选题：可见光 + 吲哚　；参考：《淮北师范大学》2017年硕士论文

【摘要】：吲哚是一种非常重要的含氮杂环化合物,广泛存在于天然产物和药物中,具有重要的生物活性和广泛的用途,正因为如此,其合成方法一直受到化学家的关注。在过去的几年里,可见光催化在有机化学领域取得了很大的突破。最近,可见光促进的无光敏化剂的有机合成反应也相继被报道,并逐渐成为有机化学领域中一个热点。本文主要围绕可见光促进的吲哚环的构建及其官能化反应开展了相关的研究工作,具体如下:1.在可见光照射下,由2-炔基苯胺与二硫醚(二硒醚)合成3-硫基吲哚或3-硒基吲哚化合物的氧化环化反应。该反应在室温,双氧水的存在下,即可通过一锅法构建吲哚类化合物。值得一提的是,该反应在无过渡金属和光催化剂的条件下,即可以中等以上产率及良好的官能团兼容性得到目标产物,与传统合成方法相比,该反应体系条件简单,绿色环保。2.在温和的条件下,通过可见光照射,实现了吲哚或N-取代吲哚与苯甲酰甲酸的脱羧偶联反应。这是一种简单且有效合成3-酰化吲哚的方法。该反应与现有合成3-酰化吲哚的方法相比,具有以下几个优点,例如:使用廉价的,易降解的有机染料孟加拉玫瑰红(rose bengal)作为光催化剂;乙醇作为低毒性溶剂;具有高的区域选择性和良好的官能团兼容性。
[Abstract]:Indole is a very important nitrogen-containing heterocyclic compound, which widely exists in natural products and drugs, and has important biological activity and wide application. Because of this, the synthetic method of indole has been paid much attention by chemists.In the past few years, visible light catalysis has made a great breakthrough in the field of organic chemistry.Recently, the organic synthesis reactions without Guang Min promoted by visible light have been reported one after another, and have gradually become a hot spot in the field of organic chemistry.This paper focuses on the construction and functionalization of visible light-stimulated indole ring, as follows: 1.The oxidative cyclization of 3-thioindole or 3-selenoindole was synthesized from 2-acetylaniline and disulfide (diselenoether) under visible light irradiation.At room temperature and in the presence of hydrogen peroxide, indole compounds can be synthesized by one-pot method.It is worth mentioning that under the condition of no transition metal and photocatalyst, the target product can be obtained with medium yield and good functional group compatibility. Compared with the traditional synthesis method, the reaction system is simple, green and environmentally friendly.Under mild conditions, the decarboxylation of indole or N-substituted indole with benzoyl formic acid was realized by visible light irradiation.This is a simple and effective method for the synthesis of 3-acylated indole.Compared with the existing methods for the synthesis of 3-acylated indole, the reaction has the following advantages: for example, the cheap and easily degradable organic dye, rose rose rose bengal, is used as photocatalyst, and ethanol is used as low toxic solvent.It has high regioselectivity and good functional group compatibility.
【学位授予单位】：淮北师范大学
【学位级别】：硕士
【学位授予年份】：2017
【分类号】：O626;O644.1

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