有机化学 ›› 2024, Vol. 44 ›› Issue (9): 2915-2923.DOI: 10.6023/cjoc202402008 上一篇    下一篇

研究论文

实用的化学选择性芳香取代: N-苯基苯磺酰胺的高效双硝基化合成N-(2,4-二硝基苯基)苯磺酰胺

徐小波a, 于晓a, 夏成才b,*(), 冀亚飞a,*()   

  1. a 华东理工大学药学院 制药过程化学工程研究中心 上海 200237
    b 山东第一医科大学(山东省医学科学院)药学院 济南 250117
  • 收稿日期:2024-02-09 修回日期:2024-04-01 发布日期:2024-04-30
  • 通讯作者: 夏成才, 冀亚飞
  • 基金资助:
    泰安市科技发展规划(2019GX015); 山东第一医科大学学术推广计划(2019LJ003)

Practical Chemoselective Aromatic Substitution: Highly Efficient Dinitrification of N-Phenylbenzenesulfonamide for Synthesis of N-(2,4-dinitrophenyl)benzenesulfonamide

Xiaobo Xua, Xiao Yua, Chengcai Xiab(), Yafei Jia()   

  1. a Engineering Research Center of Pharmaceutical Process Chemistry; School of Pharmacy, East China University of Science and Technology, Shanghai 200237
    b School of Pharmaceutical Sciences & Institute of Materia Medica, Shandong First Medical University & Shandong Academy of Medical Sciences, Jinan 250117
  • Received:2024-02-09 Revised:2024-04-01 Published:2024-04-30
  • Contact: Chengcai Xia, Yafei Ji
  • Supported by:
    Science and Technology Development Plan of Tai'an City(2019GX015); Academic Promotion Program of Shandong First Medical University(2019LJ003)

N-苯基苯磺酰胺为原料, 经双硝基化反应合成了N-(2,4-二硝基苯基)苯磺酰胺. 该方法操作方便, 具有良好的官能团耐受性. 该反应可能经过二氧化氮自由基(NO2•)中间体, 该中间体由硝酸钠和过硫酸铵的热反应过程产生. 此外, 该方法还为合成苯并咪唑和喹喔啉衍生物的关键中间体2,4-二硝基苯胺衍生物的制备提供了直接途径.

关键词: N-苯基苯磺酰胺, 双硝基化, N-(2,4-二硝基苯基)苯磺酰胺

A novel route for dinitrification of N-phenylbenzenesulfonamide to synthesize N-(2,4-dinitrophenyl)benzenesul- fonamide has been developed. The method features convenient operation and good functional group tolerance. This reaction may go through a nitrogen dioxide radical (NO2•) intermediate, which is generated by the thermal reaction process of sodium nitrate and ammonium persulfate. In addition, it provides direct approach for the preparation of 2,4-dinitroaniline derivatives which are crucial intermediate for the synthesis of benzimidazoles and quinoxaline derivatives.

Key words: N-phenylbenzenesulfonamide, dinitrification, N-(2,4-dinitrophenyl)benzenesulfonamide