碱促进直接合成3-烷氧基甲基吲哚衍生物的研究
发布时间：2018-08-28 17:09
【摘要】：由于C-H键直接官能团化反应与传统方法相比具有高效、原子经济性、步骤简单、成本低廉等优势,近年来得到化学家的广泛关注,并成功地应用于药物分子、天然产物和功能材料的合成。大多数有机分子含有多个C-H键,选择性地对特定位置上C-H键进行官能团转化,合成高附加值的目标产物是该领域的一个棘手问题,化学家通过在底物中引入诱导基成功地解决了该问题。此外,杂环化合物中杂原子的存在使得分子中C-H键活性存在明显差异,无需导向基团既可以实现特定位置的区域官能团化,利用这一性质,科学家们实现了大量的杂环化合物的区域选择性官能团化反应。另外,吲哚广泛地存在于生物活性分子和天然产物中,并且是重要的有机合成中间体,因此关于吲哚衍生物的合成方法研究一直是有机化学家研究的热点之一。本论文主要研究了通过多分子串联反应,以简单吲哚、醛和醇为底物,碱促进一锅法合成3-烷氧基甲基吲哚衍生物(Scheme 1)。该方法高效、快捷、成本低廉、原料易得,并且无需添加过渡金属及其他的添加剂。依据实验结果及相关文献报道,推测反应机理如下(Scheme 2):
[Abstract]:Because C-H bond direct functional reaction has the advantages of high efficiency, atomic economy, simple steps and low cost compared with traditional methods, it has been widely concerned by chemists in recent years, and has been successfully applied to drug molecules. Synthesis of natural products and functional materials. Most organic molecules contain multiple C-H bonds. The selective conversion of C-H bonds to specific sites and the synthesis of target products with high added value are a thorny problem in this field. Chemists successfully solved the problem by introducing inducers into the substrate. In addition, the presence of hetero atoms in heterocyclic compounds makes the C-H bond activity in the molecule significantly different. Scientists have achieved a large number of heterocyclic compounds of regioselective functional reactions. In addition, indole widely exists in bioactive molecules and natural products, and is an important intermediate of organic synthesis. Therefore, the research on the synthetic methods of indole derivatives has been one of the hot spots of organic chemists. In this paper, the synthesis of 3-alkoxy methyl indole derivative (Scheme _ 1) in one pot with simple indole, aldehyde and alcohol in series reaction was studied. The method is efficient, fast, low cost, easy to obtain raw materials and does not need to add transition metal and other additives. According to the experimental results and related literature reports, the mechanism of the reaction is as follows (Scheme 2):
【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
本文编号：2210031
[Abstract]:Because C-H bond direct functional reaction has the advantages of high efficiency, atomic economy, simple steps and low cost compared with traditional methods, it has been widely concerned by chemists in recent years, and has been successfully applied to drug molecules. Synthesis of natural products and functional materials. Most organic molecules contain multiple C-H bonds. The selective conversion of C-H bonds to specific sites and the synthesis of target products with high added value are a thorny problem in this field. Chemists successfully solved the problem by introducing inducers into the substrate. In addition, the presence of hetero atoms in heterocyclic compounds makes the C-H bond activity in the molecule significantly different. Scientists have achieved a large number of heterocyclic compounds of regioselective functional reactions. In addition, indole widely exists in bioactive molecules and natural products, and is an important intermediate of organic synthesis. Therefore, the research on the synthetic methods of indole derivatives has been one of the hot spots of organic chemists. In this paper, the synthesis of 3-alkoxy methyl indole derivative (Scheme _ 1) in one pot with simple indole, aldehyde and alcohol in series reaction was studied. The method is efficient, fast, low cost, easy to obtain raw materials and does not need to add transition metal and other additives. According to the experimental results and related literature reports, the mechanism of the reaction is as follows (Scheme 2):
【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
【参考文献】
相关期刊论文 前2条
1 Yang Zheng;Ren-Jun Li;Zhen Zhan;Yan Zhou;Li Hai;Yong Wu;;Fe-catalyzed regioselective Friedel Crafts hydroxyalkylation of N-substituted glyoxylamide with indoles[J];Chinese Chemical Letters;2016年01期
2 卢贝丽;李现艳;林咏梅;;过渡金属催化的C—H键官能团化构建吲哚结构的研究进展[J];有机化学;2015年11期
，本文编号：2210031
本文链接：https://www.wllwen.com/kejilunwen/huaxue/2210031.html
教材专著
