有机化学 ›› 2019, Vol. 39 ›› Issue (8): 2270-2276.DOI: 10.6023/cjoc201902029 上一篇    下一篇

所属专题: 陈茹玉先生诞辰100周年

研究论文

一锅法合成2-(2-氨基苯甲酰胺基)苯甲酸类化合物

万琳茜a,b, 高峰a, 陈伟a, 周先礼a,b   

  1. a 西南交通大学生命科学与工程学院 成都 610031;
    b 西南交通大学材料先进技术教育部重点实验室 成都 610031
  • 收稿日期:2019-02-25 修回日期:2019-04-17 出版日期:2019-08-25 发布日期:2019-05-10
  • 通讯作者: 陈伟, 周先礼 E-mail:chenweicstq@163.com;zhouxl@swjtu.edu.cn
  • 基金资助:

    国家自然科学基金(No.81773605)、四川省科技计划(No.2018JY0077)和西南交通大学前沿交叉基础研究(No.2682017QY04)资助项目.

One-Pot Synthesis of 2-((2-Aminobenzoyl)amino)benzoic Acid Derivatives

Wan Linxia,b, Gao Fenga, Chen Weia, Zhou Xianlia,b   

  1. a School of Life Science and Engineering, Southwest Jiaotong University, Chengdu 610031;
    b Key Laboratory of Advanced Technology of Materials, Ministry of Education, Southwest Jiaotong University, Chengdu 610031
  • Received:2019-02-25 Revised:2019-04-17 Online:2019-08-25 Published:2019-05-10
  • Contact: 10.6023/cjoc201902029 E-mail:chenweicstq@163.com;zhouxl@swjtu.edu.cn
  • Supported by:

    Project supported by the National Natural Science Foundation of China (No. 81773605), the Science and Technology Project of Sichuan Province (No. 2018JY0077), and the Interdisciplinary Frontier Basic Research Project of Southwest Jiaotong University (No. 2682017QY04).

报道了一种一锅法高效合成2-(2-氨基苯甲酰胺基)苯甲酸类化合物的新方法.以取代2-氨基苯甲酸为原料,合成了20个2-(2-氨基苯甲酰胺基)苯甲酸类化合物,其中有9个新化合物,收率达84%~99%.该方法操作简单,反应条件温和,对环境友好,产率高,并且底物普适性好.探讨了电子效应和空间位阻因素对反应的影响,为2-(2-氨基苯甲酰胺基)苯甲酸类化合物的合成提供了一种新途径.并且,2-(2-氨基苯甲酰胺基)苯甲酸(3a)经一步反应可高效生成大环内酯4和喹唑啉酮5.

关键词: 2-(2-氨基苯甲酰胺基)苯甲酸, 2-氨基苯甲酸, 一锅法

An efficient and one-pot method for the preparation of 2-((2-aminobenzoyl)amino)benzoic acid derivatives has been reported. Twenty 2-((2-aminobenzoyl)amino)benzoic acid derivatives were prepared with 84%~99% yields and nine compounds are new compounds. The effects of electron effect and steric hindrance on the reaction were discussed. It provides an operationally simple, environmentally friendly, high yield and good substrate universality method for the synthesis of 2-(2-aminobenzamide)benzoic acid derivatives. Furthermore, macrolide 4 and quinazolinone 5 can be synthesized from 2-((2-ami-nobenzoyl)amino)benzoic acid (3a) in one-step over 92% yields.

Key words: 2-((2-aminobenzoyl) amino) benzoic acid, 2-aminobenzoic acid, one-pot synthesis