邻炔酰胺基苯甲酸酯的合成+文献综述
毕业论文关键词：异香豆素；含氮取代基的异香豆素；邻炔(烯)酰胺(胺)苯甲酸酯底物
Study on Synthesis of ortho alkyne amide benzoate
Abstract:The study foud that the synthesis of isocoumarin derivatives with nitrogen functional groups can be achieved by the cyclization reaction of adjacent alkynyl benzoic acid derivatives. Thus, synthesis of oalkynyl (ene) amide (amine) benzoate substrate in a convenient, eco-friendly, low cost, mild conditions, and efficient route is important for the research of isocoumarin having nitrogen functional groups.In this article, we have designed a 5-steps synthesis process of acetylene amide benzoate: The first step in a solvent and the catalyst system by a substitution reaction on the reactive H benzylamine substituent protected with a Ts. The second step, the use of TMS acetylene Sonogashira coupling reaction with 2-iodo-benzoic acid methyl ester coupled together. The third step, with a potassium carbonate removal of TMS. The fourth step in the methyl formate solution of silver nitrate, the terminal alkyne with NBS hydrogen bromide. A fifth step in the electrophilic attack copper sulfate catalyzed modification of the final substitution, to give the desired o-alkynyl amido benzoate. By a total of 5-step reaction, the total yield is 76.68%.
KeyWords: Isocoumarin; A nitrogen-containing substituent isocoumarin； Adjacent alkyne (EN) amide (amine) benzoic acid ester substrates
目录
1 前言 1
1.1 异香豆素衍生物概述 1
1.2 异香豆素类化合物的生物活性研究进展 1
1.3异香豆素衍生物的合成研究进展 2
1.3.1二氢异香豆素类化合物的合成 2
1.3.2多取代异香豆素的合成 2
1.4 本课题的研究内容和研究意义 3
2 邻炔酰胺基苯甲酸酯的合成研究 5
2.1 合成路线设计思路 5
2.2 使用的材料试剂、仪器设备 7
2.2.1 主要化学原料与试剂 7
2.2.2 仪器设备 7
2.3苄胺上Ts保护 8
2.3.1 反应方程式 8
2.3.2 实验步骤 8
2.3.3 实验注意事项 9
2.4 Sonogashira 偶联 9
2.4.1 反应方程式 9
2.4.2 实验步骤 9
2.4.3 实验注意事项 9
2.5 脱TMS保护 9
2.5.1 反应方程式 9
2.5.2 实验步骤 10
2.5.3 实验注意事项 10
2.6 末端炔氢溴化 10
2.6.1 反应方程式 10
2.6.2 实验步骤 10
2.6.3 实验注意事项 10
2.7胺的取代 10
2.7.1 反应方程式 10