SIOC English
有机化学
高级检索

有机化学 >

2024 , Vol. 44 >Issue 9: 2915 - 2923

DOI: https://doi.org/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 ,
  • 于晓 ,
  • 夏成才 ,
  • 冀亚飞
展开
  • 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

  网络出版日期: 2024-04-30

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)

收起

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

  • Xiaobo Xu ,
  • Xiao Yu ,
  • Chengcai Xia ,
  • Yafei Ji
Expand
  • 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
*E-mail: ;

Received date: 2024-02-09

  Revised date: 2024-04-01

  Online published: 2024-04-30

Supported by

Science and Technology Development Plan of Tai'an City(2019GX015); Academic Promotion Program of Shandong First Medical University(2019LJ003)

Fold

摘要

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

本文引用格式

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, 2024 , 44(9) : 2915 -2923 . DOI: 10.6023/cjoc202402008

Abstract

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

参考文献

[1]
Chen, J.; Przyuski, K.; Roemmele, R.; Bakale. R. P. Org. Process Res. Dev. 2011, 15, 1063.
[2]
Burke, J. A.; Garst, M. E.; Wheeler, L. WO 2000038684, 2000.
[3]
Wallace, E. M.; Lyssikatos, J. P.; Hurley, B. T.; Marlow, A. L. WO 2003077914, 2003.
[4]
Qiu, J.-J.; Xiao, J.-Q.; Tang, B.-T.; Ju, B.-Z.; Zhang, S.-F. Dyes Pigm. 2019, 160, 524.
[5]
(a) Tang, Z.-Y.; Feng, Y.-B.; Xu, B.; Luo, Y.; Zou, H.-K.; Liu, B.-L.; Chen, J.-F.; Chu, G.-W.; Chen, X.-D.; Xu, W.-F.; Sun, B.-C.; Zhang. L.-L. CN 115594595, 2023.
[5]
(b) Liu, Z.-W.; Wang, Y.-Q.; Wang, L.-L.; Zhang, S.-F.; Li, B.-L.; Wang. J.-T. CN 113214088, 2021.
[6]
Tasneem; Ali, M. M.; Rajanna, K. C.; Saiparakash, P. K. Synth. Commun. 2001, 31, 1123.
[7]
Wu, L.-Q.; Yao, L.-F.; Yin, W.-Y.; Yu, J.-X. Synthesis 2023, 55, 3104.
[8]
(a) Ma, X.-M.; Li, B.-D; Lu, M.; Lv, C.-X. Chin. Chem. Lett. 2012, 23, 73.
[8]
(b) Ma, X.-M.; Li, B.-D; Lu, M.; Lv, C.-X. Chin. Chem. Lett. 2012, 23, 809.
[8]
(c) Wan, Y.-M.; Zhang, Z.-G.; Ma, N.-N.; Bi, J.-J; Zhang, G.-S. J. Org. Chem. 2019, 84, 780.
[8]
(d) Botla, V.; Ramana, D. V.; Chiranjeevi, B.; Chandrasekharam, M. ChemistrySelect 2016, 1, 3974.
[8]
(e) Gao, Y.; Mao, Y.-Y.; Zhang, B.-W.; Zhan, Y.-Y.; Huo, Y.-P. Org. Biomol. Chem. 2018, 16, 3881.
[8]
(f) Lu, Y.; Li, Y. M.; Zhang, R.; Jin, K.; Duan, C.-Y. Tetrahedron 2013, 69, 9422.
[8]
(g) Ji, Y.-F.; Yan, H.; Jiang, Q. -B. Eur. J. Org. Chem. 2015, 2051.
[8]
(h) Hernando, E.; Castillo, R. R.; Rodriguez, N.; Arrayas, R. G.; Carretero, J. C. Chem.-Eur. J. 2014, 20, 13854.
[8]
(i) Vinayak, B.; Chandrasekharam, M. Org. Lett. 2017, 19, 3528.
[8]
(j) Dai, E.; Dong, Y.-R., Kong, R.; Liu, G.-Z.; Dong, Y.; Wu, Q.; Liang, D.-Q.; Ma, Y.-H. Synth. Commun. 2020, 50, 1687.
[8]
(k) Wang, Y.-L.; Zhang, L.-B.; Niu, J.-L.; Song, M.-P. Chin. J. Org. Chem. 2019, 39, 1761 (in Chinese).
[8]
(王云龙; 张林宝; 牛俊龙; 宋毛平, 有机化学, 2019, 39, 1761.)
[9]
(a) Wang, S.-F.; Zhao, Q.-P.; Wang, G.-D.; Wang, K.; Xia. C.-C. Chin. J. Org. Chem. 2018, 38, 1849 (in Chinese).
[9]
(王少凡; 赵启鹏; 王国栋; 王凯; 夏成才, 有机化学, 2018, 38, 1849.)
[9]
(b) Wang, G.-D.; Sun, J.; Wang, K.; Han, J.-F.; Li, H.-S.; Duan, G.-Y.; You, G.-R.; Li, F.-R.; Xia, C.-C. Org. Chem. Front. 2019, 6, 1608.
[9]
(c) Hao, L.-Q.; Wang, G.-D.; Sun, J.; Xu, J.; Li, H.-S.; Duan, G.-Y.; Xia, C.-C.; Zhang, P.-F. Adv. Synth. Catal. 2020, 362, 1657.
[9]
(d) Yu, X.; Zhu, W.-J.; Liu, H.-Y.; Liu, Y.; Li, H.-S.; Han, J.-F.; Duan, G.-Y.; Bai, Z.-S.; Zhang, P.-F.; Xia. C.-C. Org. Biomol. Chem. 2022, 20, 5444.
[10]
Javorskis, T.; Orentas, E. J. Org. Chem. 2017, 82, 13423.
[11]
Yu, X.; Ma, Z.-H.; Zhu, W.-J.; Liu, H.-Y.; Zhang, Z.-H.; Liu, Y.; Zhang, M.; Zhao, J.-B.; Zhang, P.-F.; Xia, C.-C. J. Org. Chem. 2022, 87, 14738.
[11]
(b) Gaba, M.; Singh, D.; Singh, S.; Sharma, V.; Gaba, P. Eur. J. Med. Chem. 2010, 45, 2245.
[12]
Badr, M. Z. A.; Aly, M. M.; Fahmy, A. M. J. Org. Chem. 1981, 46, 4784.
Options
文章导航

/

〈 〉