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

doi:10.6023/cjoc202402008

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,*

^a华东理工大学,药学院,制药过程化学工程研究中心上海市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

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

Xiaobo Xu^a, Xiao Yu^a, Chengcai Xia^b,*, Yafei Ji^a,*

^aEngineering Research Center of Pharmaceutical Process Chemistry, Ministry of Education; School of Pharmacy, East China University of Science and Technology Shanghai 200237;
^bSchool 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
Contact: * E-mail: jyf@ecust.edu.cn & xiachc@163.com
Supported by:
Science and Technology Development Plan of Tai'an City (2019GX015), the Academic promotion program of Shandong First Medical University (nos.2019LJ003).

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摘要/Abstract

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 (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 of 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 (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

引用此文

徐小波, 于晓, 夏成才, 冀亚飞. 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[J]. 有机化学, doi: 10.6023/cjoc202402008.

Xiaobo Xu, Xiao Yu, Chengcai Xia, Yafei Ji. Practical Chemoselective Aromatic Substitution: Highly Efficient Dinitrification of N-phenylbenzenesulfonamide for Synthesis of N-(2,4-dinitrophenyl)benzenesulfonamide[J]. Chinese Journal of Organic Chemistry, doi: 10.6023/cjoc202402008.

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