Citation: Hao Wenyan, Wang Yuyun, Liu Yunyun. Catalyst-Free Selective C5-H Bromination and Chlorination of 8-Amido Quinolines[J]. Chinese Journal of Organic Chemistry, ;2017, 37(12): 3198-3203. doi: 10.6023/cjoc201705041 shu

Catalyst-Free Selective C5-H Bromination and Chlorination of 8-Amido Quinolines

  • Corresponding author: Hao Wenyan, wenyanhao@jxnu.edu.cn
  • Received Date: 28 May 2017
    Revised Date: 18 July 2017
    Available Online: 30 December 2017

    Fund Project: the Scientific Research Fund of Jiangxi Provincial Education Department GJJ160285Project supported by the National Natural Science Foundation of China (Nos. 21562024, 21762023), and the Scientific Research Fund of Jiangxi Provincial Education Department (No. GJJ160285)the National Natural Science Foundation of China 21762023the National Natural Science Foundation of China 21562024

Figures(2)

  • A simple and efficient selective halogenation (Cl, Br) reaction in the C5 position of 8-amidoquinolines has been developed via catalyst free C-H bond elaboration. This facile synthetic method shows good substrate tolerance and most of the halogenated products were obtained with excellent yield.
  • 加载中
    1. [1]

      (a) Solomon, V. R. ; Lee, H. Curr. Med. Chem. 2011, 18, 1488.
      (b) Liu, G. ; Yi, M. ; Liu, L. ; Wang, J. ; Wang, J. Chem. Commun. 2015, 51, 2911.

    2. [2]

      Wan, J.; Y. Jing, Y.; Wei, L. Asian J. Org. Chem. 2017, 6, 668.

    3. [3]

      Gharpure, S. J.; Nanda, S. K.; Adate, P. A.; Shelke, Y. G. J. Org. Chem. 2017, 82, 2067.  doi: 10.1021/acs.joc.6b02896

    4. [4]

      Ali, W.; Dahiya, A.; Pandey, R.; Alam, T.; Patel, B. K. J. Org. Chem. 2017, 82, 2089.  doi: 10.1021/acs.joc.6b02912

    5. [5]

      Tobisu, M.; Hyodo, I.; Chatani, N. J. Am. Chem. Soc. 2009, 131, 12070.  doi: 10.1021/ja9053509

    6. [6]

      Sun, K.; Lv, Y.; Wang, J.; Sun, J.; Liu, L.; Jia, M.; Liu, X.; Z. Li, Z.; Wang, X. Org. Lett. 2015, 17, 4408.  doi: 10.1021/acs.orglett.5b01857

    7. [7]

      Berman, A. M.; Lewis, J. C.; Bergman, R. G.; Ellman, J. A. J. Am. Chem. Soc. 2008, 130, 14926.  doi: 10.1021/ja8059396

    8. [8]

      Boudet, N.; Lachs, J. R.; Knochel, P. Org. Lett. 2007, 9, 5525.  doi: 10.1021/ol702494k

    9. [9]

      (a) Cong, X. ; Zeng, X. Org. Lett. 2014, 16, 3716.
      (b) Reddy, M. D. ; Fronczek, F. R. ; Watkins, E. B. Org. Lett. 2016, 18, 5620.
      (c) Chen, H. ; Li, P. ; Wang, M. ; Wang, L. Org. Lett. 2016, 18, 4794.
      (d) Kuninobu, Y. ; Nishia, M. ; Kanai, M. Org. Biomol. Chem. 2016, 14, 8092.
      (e) Shen, C. ; Xu, J. ; Beibei Ying, B. ; Zhang, P. ChemCatChem 2016, 8, 3557.
      (f) Zhang, J. ; Hao, X. ; Wang, Z. ; Ren, C. ; Niu, J. ; Song, M. Chin. J. Org. Chem. 2017, 37, 1237.
      (g) Luo, F. ; Long, Y. ; Li, Z. ; Zhou, X. Acta Chim. Sinica 2016, 74, 805.

    10. [10]

      (a) Ji, D. ; He, X. ; Xu, Y. ; Xu, Z. ; Bian, Y. ; Liu, W. ; Zhu, Q. ; Xu, Y. Org. Lett. 2016, 18, 4478.
      (b) Whiteoak, C. J. ; Planas, O. ; Company, A. ; Ribasa, X. Adv. Synth. Catal. 2016, 358, 1679.
      (c) He, Y. ; Zhao, N. ; Qiu, L. ; Zhang, X. ; Fan, X. Org. Lett. 2016, 18, 6054.
      (d) Dou, Y. ; Xie, Z. ; Sun, Z. ; Fang, H. ; Shen, C. ; Zhang, P. ; Qing Zhu, Q. ChemCatChem 2016, 8, 3570.
      (e) Sahoo, H. ; Kesava, M. ; Ramakrishna, R. ; Baidya, M. Chem. -Eur. J. 2016, 22, 1592.

    11. [11]

      (a) Liang, H. ; Jiang, K. ; Ding, W. ; Yuan, Y. ; Shuai, Li. ; Chen, Y. ; Ye Wei, Y. Chem. Commun. 2015, 51, 16928.
      (b) Qiao, H. ; Sun, S. ; Yang, F. ; Zhu, Y. ; Zhu, W. ; Dong, Y. ; Wu, Y. ; Kong, X. ; Jiang, L. ; Wu, Y. Org. Lett. 2015, 17, 6086.
      (c) Wei, J. ; Jiang, J. ; Xiao, X. ; Lin, D. ; Deng, Y. ; Ke, Z. ; Jiang, H. ; Zeng, W. J. Org. Chem. 2016, 81, 946.
      (d) Xu, J. ; Shen, C. ; Zhu, X. ; Zhang, P. ; Ajitha, M. J. ; Huang, K. ; An, Z. ; Liu, X. Chem. Asian J. 2016, 11, 882.
      (e) Zhu, L. ; Qiu, R. ; Cao, X. ; Xiao, S. ; Xu, X. ; Au, C. ; Yin, S. Org. Lett. 2015, 17, 5528.

    12. [12]

      (a) Suess, A. M. ; Mehmed Z. Ertem, M. Z. ; Cramer, C. J. Stahl, S. S. J. Am. Chem. Soc. 2013, 135, 9797.
      (b) Guo, H. ; Chen, M. ; Jiang, P. ; Chen, J. ; Pan, L. ; Wang, M. ; Xie, C. ; Zhang, Y. Tetrahedron 2015, 71, 70.
      (c) Liu, X. ; Wu, Z. ; Luo, X. ; He, Y. ; Zhou, X. ; Fan, Y. ; Huang, G. RSC Adv. 2016, 6, 71485.
      (d) Xu, J. ; Zhu, X. ; Zhou, G. ; Ying, B. ; Ye, P. ; Su, L. ; Shen, C. ; Zhang, P. Org. Biomol. Chem. 2016, 14, 3016.
      (e) Khan, B. ; Ruchir Kant, R. ; Koley, D. Adv. Synth. Catal. 2016, 358, 2352.
      (f) Wu, C. ; Zhou, H. ; Wu, Q. ; He, M. ; Li, P. ; Su, Q. ; Mu, Y. Synlett. 2016, 27, A~H.
      (g) Sahoo, H. ; Ramakrishna, I. ; Baidya, M. Chem. Select 2016, 1, 1949.
      (h) He, X. ; Xu, Y. ; Kong, L. ; Wu, H. ; Ji, D. ; Wang, Z. ; Xu, Y. ; Zhu, Q. Org. Chem. Front. 2017, 4, 1046.
      (i) Rao, N. S. ; Reddy, G. M. ; Sridhar, B. ; Sarma, M. S. Eur. J. Org. Chem. 2017, 438.

    13. [13]

      Sun, M.; Sun, S.; Qiao, H.; Yang, F.; Zhu, Y.; Kang, J.; Wu, Y.; Wu, Y. Org. Chem. Front. 2016, 3, 1646.  doi: 10.1039/C6QO00379F

    14. [14]

      Xia, C.; Wang, K.; Xu, J.; Shen, C.; Sun, D.; Li, H.; Wang, G.; Zhang, P. Org. Biomol. Chem., 2017, 15, 531.  doi: 10.1039/C6OB02375D

    15. [15]

      (a) Abouelhassan, Y. ; Garrison, V. G. ; Burch, M. ; Wong, W. ; Norwood, V. M. ; Huigens, R. W. Bioorg. Med. Chem. Lett. 2014, 24, 5076.
      (b) Liu, Y. -C. ; Wei, J. -H. ; Chen, Z. -F. ; Liu, M. ; Gu, Y. -Q. ; Huang, K. -B. ; Li, Z. -Q. ; Liang, H. Eur. J. Med. Chem. 2013, 69, 554.
      (c) Tardito, S. ; Barilli, A. ; Bassanetti, I. ; Tegoni, M. ; Bussolati, O. ; Franchi-Gazzola, R. ; Mucchino, C. ; Marchio, L. J. Med. Chem. 2012, 55, 10448.
      (d) Bhat, S. ; Shim, J. S. ; Zhang, F. ; Chong, C. R. ; Liu, J. O. Org. Biomol. Chem. 2012, 10, 2979.
      (e) Madrid, P. B. ; Sherrill, J. ; Liou, A. P. ; Weisman, J. L. ; Derisi, J. L. ; Guy, R. K. Bioorg. Med. Chem. Lett. 2005, 15, 1015.

    16. [16]

      (a) Jiang, H. ; Taggart, H. ; Zhang, X. ; Benbrook, D. M. ; Lind, S. E. ; Ding, W. -Q. Cancer Lett. 2011, 312, 11.
      (b) Heidary, D. K. ; Howerton, B. S. ; Glazer, E. C. J. Med. Chem. 2014, 57, 8936.

    17. [17]

      During the preparation of our manuscript, a water-mediated C5-H halogenations of 8-amidoquinolines has been reported. Chen, J. ; Wang, T. ; Liu, Y. ; Wang, T. ; Lin, A. ; Yao, H. ; Xu, J. Org. Chem. Front. 2017, 4, 622.

    18. [18]

      Hao, W.-Y.; Liu, Y.-Y. Beilstein J. Org. Chem. 2015, 11, 2132.  doi: 10.3762/bjoc.11.230

    19. [19]

      Menini, L.; da Cruz Santos, J. C.; Gusevskaya, E. V. Adv. Synth. Catal. 2008, 350, 2052.  doi: 10.1002/adsc.v350:13

    20. [20]

      Wang, Y.; Wang, Y.; Jiang, K.; Zhang, Q.; Li, D. Org. Biomol. Chem. 2016, 14, 10180.  doi: 10.1039/C6OB02079H

    21. [21]

      Qiao, H. J.; Sun, S. Y.; Yang, F.; Zhu, Y.; Kang, J. X.; Wu, Y. S.; Wu, Y. J. Adv. Synth. Catal. 2017, 359, 1976.  doi: 10.1002/adsc.v359.11

  • 加载中
    1. [1]

      Min Yan , Zihao Ye , Ping Lu . Catalyst-free, visible-light-induced [2π + 2σ] cycloaddition towards azabicyclohexanes. Chinese Chemical Letters, 2025, 36(6): 110540-. doi: 10.1016/j.cclet.2024.110540

    2. [2]

      Xiaoping Zhang , Xiaoyun Wang , Liqun Cheng , Lijuan Liu , Jianchuan Liu , Jianhua Ding , Roman Balabin , Xinglei Zhang , Konstantin Chingin , Huanwen Chen . Catalyst-free production of hydrogen peroxide enabled by plasma-microdroplet-generated water radical cations. Chinese Chemical Letters, 2026, 37(12): 112774-. doi: 10.1016/j.cclet.2026.112774

    3. [3]

      Gang Hu , Chun Wang , Qinqin Wang , Mingyuan Zhu , Lihua Kang . The controlled oxidation states of the H4PMo11VO40 catalyst induced by plasma for the selective oxidation of methacrolein. Chinese Chemical Letters, 2025, 36(2): 110298-. doi: 10.1016/j.cclet.2024.110298

    4. [4]

      Xiangyang Ji , Yishuang Chen , Peng Zhang , Shaojia Song , Jian Liu , Weiyu Song . Boosting the first C–H bond activation of propane on rod-like V/CeO2 catalyst by photo-assisted thermal catalysis. Chinese Chemical Letters, 2025, 36(5): 110719-. doi: 10.1016/j.cclet.2024.110719

    5. [5]

      Haoran Shi , Jiaxin Wang , Yuqin Zhu , Hongyang Li , Guodong Ju , Lanlan Zhang , Chao Wang . Highly selective α-C(sp3)-H arylation of alkenyl amides via nickel chain-walking catalysis. Chinese Chemical Letters, 2024, 35(7): 109333-. doi: 10.1016/j.cclet.2023.109333

    6. [6]

      Wei-Bin Li , Xiao-Chao Huang , Pei Liu , Jie Kong , Guo-Ping Yang . Recent advances in directing group assisted transition metal catalyzed para-selective C-H functionalization. Chinese Chemical Letters, 2025, 36(6): 110543-. doi: 10.1016/j.cclet.2024.110543

    7. [7]

      Xin-Juan Wang , Yao-Hang Cheng , Xin-Yan Lv , Li-Ye Liang , Guang-Hui An , Guang-Ming Li . Ruthenium-catalyzed alkylarylation of alkenes via para-selective C-H functionalization of unprotected anilines. Chinese Chemical Letters, 2026, 37(8): 112154-. doi: 10.1016/j.cclet.2025.112154

    8. [8]

      Wanqiu Zhao , Aijia Zhang , Qingyun Huang , Pingping Tang . Selective meta-C-H trifluoromethylation of pyridines via 1,4-dihydropyridinephosphonate. Chinese Chemical Letters, 2026, 37(9): 112133-. doi: 10.1016/j.cclet.2025.112133

    9. [9]

      Tianxia Chen , Yunhui Chen , Weiwei Li , Peipei Cen , Yan Guo , Jin Zhang , Cunding Kong , Xiangyu Liu . Fabricating AuAg-nanoparticles/ZIF-8 composites for selective detection and efficient extraction of dinitroaniline pesticides. Chinese Chemical Letters, 2025, 36(8): 110214-. doi: 10.1016/j.cclet.2024.110214

    10. [10]

      Xiaoqiang Wang , Fangyuan Zhou , Yue Liu , Zhongbiao Wu . CePO4 supported Cr catalyst with superior sulfur tolerance for selective catalytic oxidation of ammonia. Chinese Chemical Letters, 2025, 36(7): 110420-. doi: 10.1016/j.cclet.2024.110420

    11. [11]

      Min Liu , Di Wang , Zenghui Ye , Donghao Jiang , Bencan Tang , Yanqi Wu , Fengzhi Zhang . Highly stereo- and enantio-selective synthesis of spiro cyclopropyl oxindoles via organic catalyst-mediated cyclopropanation. Chinese Chemical Letters, 2025, 36(10): 110923-. doi: 10.1016/j.cclet.2025.110923

    12. [12]

      Shuo Li , Xinran Liu , Yongjie Zheng , Jun Ma , Shijie You , Heshan Zheng . Effective peroxydisulfate activation by CQDs-MnFe2O4@ZIF-8 catalyst for complementary degradation of bisphenol A by free radicals and non-radical pathways. Chinese Chemical Letters, 2024, 35(5): 108971-. doi: 10.1016/j.cclet.2023.108971

    13. [13]

      Cui-Ting Yang , Dan-Dan Wang , Shuai Chen , Jian-Mei Yang , Jun-Nan He , Jun-Hui Zhang , Xiao-Qing Liu , Jin Zhang , Lei Zhang , Yan Zhao . A chiral supramolecular nanocatcher prepared by d-biotin-pillar[5]arene for the selective capture and targeted delivery of oxaliplatin enantiomers. Chinese Chemical Letters, 2025, 36(9): 110820-. doi: 10.1016/j.cclet.2025.110820

    14. [14]

      Deyan Wu , Qingjiang Ma , Yanquan Chen , Guofeng Yang , Fengcai Zhang , Meiyan Jiang , Xue Wang , Xingfu Liu , Qian Zhou , Yi-You Huang , Zhe Li , Hai-Bin Luo . Plasma metabolites-based drug design: Discovery of novel and highly selective phosphodiesterase 5 inhibitors. Chinese Chemical Letters, 2026, 37(5): 111236-. doi: 10.1016/j.cclet.2025.111236

    15. [15]

      Xiaodong Zhang ,  Bohui Xu ,  Deshuai Xiao ,  Xinyuan Zhang ,  Pifu Gong ,  Zheshuai Lin . From centrosymmetric CN3H6C6H5SO3 to non-centrosymmetric CN3H6C6H4SO3(OH): Hydroxyl introduced hydrogen bond reconstruction to realize strong second harmonic generation. Chinese Journal of Structural Chemistry, 2025, 44(10): 100707-100707. doi: 10.1016/j.cjsc.2025.100707

    16. [16]

      Shen Wang ,  Yi Wei ,  Weijie Li ,  Chao Han . Advances in copper-based catalysts for selective CO₂ electroreduction to C1 and C2 products. Chinese Journal of Structural Chemistry, 2026, 45(8): 100944-100944. doi: 10.1016/j.cjsc.2026.100944

    17. [17]

      Man Zhao , Liwu Qiang , Zonghang Liu , Wei Wen , Ze Wang , Qilin Guo , Yanxia Zhang , Aiqin Hao , Yuhong Chang , Junming Zhang , Baoliang Lv , Xiaofang Ma , He Xiao , Jianfeng Jia . Programming selective formation of epoxy bond: Carbon dots as multifunctional mediators for steering propylene electro oxidation pathways on Ag-graphene hybrids. Chinese Chemical Letters, 2026, 37(10): 112843-. doi: 10.1016/j.cclet.2026.112843

    18. [18]

      Guoju Guo , Xufeng Li , Jie Ma , Yongjia Shi , Jian Lv , Daoshan Yang . Photocatalyst/metal-free sequential C–N/C–S bond formation: Synthesis of S-arylisothioureas via photoinduced EDA complex activation. Chinese Chemical Letters, 2024, 35(11): 110024-. doi: 10.1016/j.cclet.2024.110024

    19. [19]

      Yuxiang Tang ,  Yong Zhang ,  Wenjun Qin ,  Xiaolin Wei ,  Yuxue Mo ,  Haiqing Zhou . Highly selective glycerol electrooxidation assisted hybrid water electrolysis using a trifunctional heterojunction CoP/(Fe0.25Co0.75)3N catalyst. Chinese Journal of Structural Chemistry, 2026, 45(7): 100922-100922. doi: 10.1016/j.cjsc.2026.100922

    20. [20]

      Ke-Ai Zhou ,  Lian Huang ,  Xing-Ping Fu ,  Li-Ling Zhang ,  Yu-Ling Wang ,  Qing-Yan Liu . Fluorinated metal-organic framework for methane purification from a ternary CH4/C2H6/C3H8 mixture. Chinese Journal of Structural Chemistry, 2023, 42(11): 100172-100172. doi: 10.1016/j.cjsc.2023.100172

Metrics
  • PDF Downloads(7)
  • Abstract views(2429)
  • HTML views(319)

通讯作者: 陈斌, bchen63@163.com
  • 1. 

    沈阳化工大学材料科学与工程学院 沈阳 110142

  1. 本站搜索
  2. 百度学术搜索
  3. 万方数据库搜索
  4. CNKI搜索
Address:Zhongguancun North First Street 2,100190 Beijing, PR China Tel: +86-010-82449177-888
Powered By info@rhhz.net

/

DownLoad:  Full-Size Img  PowerPoint
Return