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

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

作　　者：Xu Xiaobo Yu Xiao Xia Chengcai Ji Yafei 徐小波;于晓;夏成才;冀亚飞(华东理工大学药学院制药过程化学工程研究中心,上海200237;山东第一医科大学(山东省医学科学院)药学院,济南250117)

机构地区：[1]Engineering Research Center of Pharmaceutical Process Chemistry/School of Pharmacy,East China University of Science and Technology,Shanghai 200237 [2]School of Pharmaceutical Sciences&Institute of Materia Medica,Shandong First Medical University&Shandong Academy of Medical Sciences,Jinan 250117

出　　处：《有机化学》2024年第9期2915-2923,共9页Chinese Journal of Organic Chemistry

基　　金：泰安市科技发展规划(No.2019GX015);山东第一医科大学学术推广计划(No.2019LJ003)资助项目.

摘　　要：A novel route for dinitrification of N-phenylbenzenesulfonamide to synthesize N-(2,4-dinitrophenyl)benzenesulfonamide has been developed.The method features convenient operation and good functional group tolerance.This reaction may go through a nitrogen dioxide radical(NO_(2)·)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.以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(NO_(2)·)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-phenylbenzenesulfonamide dinitrification N-(2 4-dinitrophenyl)benzenesulfonamide 

分 类 号：O625.6[理学—有机化学]