Citation: Zheng Kanghe, Zhou Bingwei, Jin Hongwei, Liu Yunkui. Bifunctional Phosphine Ligand-Enabled Gold(Ⅰ)-Catalyzed Efficient Synthesis of 1, 5-Benzodiazepines[J]. Chinese Journal of Organic Chemistry, ;2020, 40(8): 2520-2525. doi: 10.6023/cjoc202003024 shu

Bifunctional Phosphine Ligand-Enabled Gold(Ⅰ)-Catalyzed Efficient Synthesis of 1, 5-Benzodiazepines

  • Corresponding author: Liu Yunkui, ykuiliu@zjut.edu.cn
  • Received Date: 9 March 2020
    Revised Date: 28 May 2020
    Available Online: 8 June 2020

    Fund Project: The Natural Science Foundation of Zhejiang Province LY20B020013Project supported by the National Natural Science Foundation of China (Nos. 21772176, 21372201), and the Natural Science Foundation of Zhejiang Province(No. LY20B020013)The National Natural Science Foundation of China 21372201The National Natural Science Foundation of China 21772176

Figures(2)

  • At room temperature, a bifunctional phosphine-gold(Ⅰ) catalyst was used to catalyze the nucleophilic addition/cyclization reaction of o-phenylenediamines with alkynes to generate 1, 5-benzodiazepines in one step. The reaction has the advantages of high atomic-economy, simple raw materials, convenient operation and mild reaction conditions.
  • 加载中
    1. [1]

      (a) Randall, L. O.; Kappel, B. In Benzodiazepines, Eds.: Garattini, S.; Mussini, E.; Randall, L. O., Raven Press, New York, 1973, p. 27.
      (b) Smalley, R. K. In Comprehensive Organic Chemistry, Eds.: Barton, D.; Ollis, W. D., Pergamon, Oxford, 1979, Vol. 4, p. 600.
      (c) Schutz, H. Benzodiazepines, Springer, Heidelberg, 1982.
      (d) Landquist, J. K. In Comprehensive Heterocyclic Chemistry, Eds.: Katritzky, A. R.; Rees, C. W., Pergamon, Oxford, 1984, Vol. 1, pp. 166~170.

    2. [2]

    3. [3]

      Fad, L. D.; Bethell, R.; Bonneau, P.; Bös, M.; Bousquet, Y.; Coordingley, M. G.; Coulombe, R.; Deroy, P.; Faucher, A.-M.; Gagnon, A.; Goudreau, N.; Grand-Maî tre, C.; Guse, I.; Hucke, O.; Kawai, S. H.; Lacoste, J.-E.; Landry, S.; Lemke, C. T.; Malenfant, E.; Mason, S.; Morin, S.; O'Meara, J.; Simoneau, B.; Titolo, S.; Yoakim, C. Bioorg. Med. Chem. Lett. 2011, 21, 398.  doi: 10.1016/j.bmcl.2010.10.131

    4. [4]

      (a) El-snyed, A. M.; Abdel-ghany, H.; El-snghier, A. M. M. Synth. Commun. 1999, 29, 3561.
      (b) Essaber, M.; Baouid, A.; Hasnaoui, A.; Benharref, A.; Lavergne, J. P. Synth. Commun. 1998, 28, 4097.
      (c) Reddy, K. V. V; Rao, P. S.; Ashok, D. Synth. Commun. 2000, 30, 1825.

    5. [5]

      (a) Pan, X.Q.; Zou, J. P.; Huang, Z. H.; Zhang, W. Tetrahedron Lett. 2008, 49, 5302.
      (b) Nardi, M.; Cozza, A.; Maiuolo, L.; Oliverio, M.; Procopio, A Tetrahedron Lett. 2011, 52, 4827 and references cited therein.
      (c) Feng, S.-E.; Xu, F.; Shen, Q. Chin. J. Chem. 2008, 26, 861.

    6. [6]

      Ried, W.; Torinus, E. Chem. Ber. 1959, 92, 2902.  doi: 10.1002/cber.19590921138

    7. [7]

      (a) Neochoritis, C. G.; Tsoleridis, C. A.; Sephanidou-Stephanatou, J.; Kontogiorgis, C. A.; Hadjipavlou-Litina, D. J. J. Med. Chem. 2010, 53, 8409.
      (b) Ha, S. K.; Shobha, D.; Moon, E.; Chari, M. A.; Mukkanti, K.; Kim, S. H.; Ahn, K. H.; Kim, S. Y. Bioorg. Med. Chem. Lett. 2010, 20, 3969.
      (c) Climent, M. J.; Corma, A.; Iborra, S.; Santos, L. L. Chem.-Eur. J. 2009, 15, 8834.

    8. [8]

      Maiti, G.; Kayal, U.; Karmakar, R.; Bhattacharya, R. N. Tetrahedron Lett. 2012, 53, 1460.  doi: 10.1016/j.tetlet.2012.01.036

    9. [9]

      Qian, J.; Liu, Y.; Cui, J.; Xu, Z. J. Org. Chem. 2012, 77, 4484.  doi: 10.1021/jo300543n

    10. [10]

      Guo, P.; Zeng, X.; Chen, S.; Luo, M. J. Organomet. Chem. 2014, 751, 438.  doi: 10.1016/j.jorganchem.2013.06.026

    11. [11]

      (a) Cai, R.; Ye, X.; Sun, Q.; He, Q.; He, Y.; Ma, S.; Shi, X. ACS Catal. 2017, 7, 1087.
      (b) Young, P. C.; Green, S. L. J.; Rosair, G. M.; Lee, A.-L. Dalton Trans. 2013, 42, 9645.

    12. [12]

      Chen, L.; Chen, K.; Zhu, S. Chem 2018, 4, 1208.  doi: 10.1016/j.chempr.2018.02.001

    13. [13]

      (a) McCahill, J. S. J.; Welch, G. C.; Stephan, D. W. Angew. Chem., Int. Ed. 2007, 46, 4968.
      (b) Stephan, D. W. Acc. Chem. Res. 2015, 48, 306.

    14. [14]

      (a) Wang, Y.; Wang, Z.; Li, Y.; Wu, G.; Cao, Z.; Zhang, L. Nat. Commun. 2014, 5, 3687.
      (b) Li, X.; Liao, S.; Wang, Z.; Zhang, L. Org. Lett. 2017, 19, 3687.
      (c) Wang, Z.; Hervieu, C.; Wong, Y.-F.; Zanoni, G.; Zhang, L. J. Am. Chem. Soc. 2017, 139, 16064.

    15. [15]

      (a) Liu, Y.; Qian, J.; Lou, S.; Xu, Z. J. Org. Chem. 2010, 75, 6300.
      (b) Liu, Y.; Qian, J.; Lou, S.; Zhu, J.; Xu, Z. J. Org. Chem. 2010, 75, 1309.
      (c) Liu, Y.; Zhu, J.; Qian, J.; Jiang, B.; Xu, Z. J. Org. Chem. 2011, 76, 9096.
      (d) Qian, J.; Liu, Y.; Zhu, J.; Jiang, B.; Xu, Z. Org. Lett. 2011, 13, 4220.
      (e) Liu, Y.; Zhu, J.; Qian, J.; Xu, Z. J. Org. Chem. 2012, 77, 5411.

    16. [16]

      Patil, V. D.; Patil, K. P.; Sutar, N. R.; Gidh, P. V. Heterocycl. Lett. 2016, 6, 61.
       

    17. [17]

      Jeganathan, M.; Pitchumani, K. ACS Sustainable Chem. Eng. 2014, 2, 1169.  doi: 10.1021/sc400560v

  • 加载中
    1. [1]

      Guilan He Yaofeng Yuan . 手性二茂铁双膦配体Xyliphos的合成及应用. University Chemistry, 2025, 40(8): 130-137. doi: 10.12461/PKU.DXHX202409122

    2. [2]

      Linjie ZHUXufeng LIU . Electrocatalytic hydrogen evolution performance of tetra-iron complexes with bridging diphosphine ligands. Chinese Journal of Inorganic Chemistry, 2025, 41(2): 321-328. doi: 10.11862/CJIC.20240207

    3. [3]

      Xiaoling LUOPintian ZOUXiaoyan WANGZheng LIUXiangfei KONGQun TANGSheng WANG . Synthesis, crystal structures, and properties of lanthanide metal-organic frameworks based on 2, 5-dibromoterephthalic acid ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(6): 1143-1150. doi: 10.11862/CJIC.20230271

    4. [4]

      Linjie ZHUXufeng LIU . Synthesis, characterization and electrocatalytic hydrogen evolution of two di-iron complexes containing a phosphine ligand with a pendant amine. Chinese Journal of Inorganic Chemistry, 2025, 41(5): 939-947. doi: 10.11862/CJIC.20240416

    5. [5]

      Yingchun ZHANGYiwei SHIRuijie YANGXin WANGZhiguo SONGMin WANG . Dual ligands manganese complexes based on benzene sulfonic acid and 2, 2′-bipyridine: Structure and catalytic properties and mechanism in Mannich reaction. Chinese Journal of Inorganic Chemistry, 2024, 40(8): 1501-1510. doi: 10.11862/CJIC.20240078

    6. [6]

      Zhiqiang Hao Jinyue Li Shiqi Zhang Yujia Hou Helue Sun . 维生素B2促进的光催化氧化合成二苯甲酮. University Chemistry, 2026, 41(5): 350-357. doi: 10.12461/PKU.DXHX202510080

    7. [7]

      Yuanyuan Ping Wangqing Kong . 光催化碳氢键官能团化合成1-苯基-1,2-乙二醇. University Chemistry, 2025, 40(6): 238-247. doi: 10.12461/PKU.DXHX202408092

    8. [8]

      Zhenhuan WangWeifei WeiRuijie MaDou LuoZhanxiang ChenJun ZhangLiyang YuGang LiZhenghui Luo . 苯并[a]苯嗪受体的核心氰基化实现高效(19.04%)绿色溶剂加工的二元有机太阳能电池. Acta Physico-Chimica Sinica, 2026, 42(2): 100182-0. doi: 10.1016/j.actphy.2025.100182

    9. [9]

      Jie ZHAOSen LIUQikang YINXiaoqing LUZhaojie WANG . Theoretical calculation of selective adsorption and separation of CO2 by alkali metal modified naphthalene/naphthalenediyne. Chinese Journal of Inorganic Chemistry, 2024, 40(3): 515-522. doi: 10.11862/CJIC.20230385

    10. [10]

      Jichao XUMing HUXichang CHENChunhui WANGLeichen WANGLingyi ZHOUXing HEXiamin CHENGSu JING . Construction and hydrogen peroxide-activated chemodynamic activity of ferrocene?benzoselenadiazole conjugate. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1495-1504. doi: 10.11862/CJIC.20250144

    11. [11]

      Xi Tan Chunhong Chen Lijia Leng Yulong Zhang . 二苯甲烷制备实验改进研究与拓展. University Chemistry, 2026, 41(5): 159-169. doi: 10.12461/PKU.DXHX202511049

    12. [12]

      Haolin Yang Aoxiang Fan Yi Song Yang Chen . 基于甲酰化-共轭脱氢串联策略的苯并呋喃-5-甲醛的制备——推荐一个基础有机合成综合性教学实验. University Chemistry, 2026, 41(5): 141-148. doi: 10.12461/PKU.DXHX202511156

    13. [13]

      Xiaoyang Li Xiaowei Huang Yimeng Zhang Huan Liu Shao Jin Junpeng Zhuang . Comprehensive Chemical Experiments on the Synthesis of 1,3-Dibromo-5,5-Dimethylhydantoin and Its Application as a Brominating Reagent. University Chemistry, 2025, 40(7): 286-293. doi: 10.12461/PKU.DXHX202408035

    14. [14]

      Mengfan Gong Dongju Zhang . Estimating Delocalization Energies of 1,3-Butadiene and Benzene with Isodesmic Reactions: A Relatively Precise Approach. University Chemistry, 2026, 41(4): 457-463. doi: 10.12461/PKU.DXHX202505036

    15. [15]

      Caixia Lin Zhaojiang Shi Yi Yu Jianfeng Yan Keyin Ye Yaofeng Yuan . Ideological and Political Design for the Electrochemical Synthesis of Benzoxathiazine Dioxide Experiment. University Chemistry, 2024, 39(2): 61-66. doi: 10.3866/PKU.DXHX202309005

    16. [16]

      Yujin DengYishuang ChenLijie ZhangHuile JinYun YangQuanlong XuShun Wang . Plasmonic Au nanobipyramid assembly covalent organic framework for boosting photocatalytic hydrogen evolution through strong local electric field. Acta Physico-Chimica Sinica, 2026, 42(6): 100193-0. doi: 10.1016/j.actphy.2025.100193

    17. [17]

      Liangzhen Hu Li Ni Ziyi Liu Xiaohui Zhang Bo Qin Yan Xiong . A Green Chemistry Experiment on Electrochemical Synthesis of Benzophenone. University Chemistry, 2024, 39(6): 350-356. doi: 10.3866/PKU.DXHX202312001

    18. [18]

      Hong RAOYang HUYicong MAChunxin LÜWei ZHONGLihua DU . Synthesis and in vitro anticancer activity of phenanthroline-functionalized nitrogen heterocyclic carbene homo- and heterobimetallic silver/gold complexes. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2429-2437. doi: 10.11862/CJIC.20240275

    19. [19]

      Yanglin JiangMingqing ChenMin LiangYige YaoYan ZhangPeng WangJianping Zhang . Experimental and Theoretical Investigations of Solvent Polarity Effect on ESIPT Mechanism in 4′-N,N-diethylamino-3-hydroxybenzoflavone. Acta Physico-Chimica Sinica, 2025, 41(2): 100012-0. doi: 10.3866/PKU.WHXB202309027

    20. [20]

      Shantao ZhangTianAo HouYandong WangZhimin FangYu WuHaolin WangTao ChenShuang ChenWenhua ZhangShengzhong (Frank) LiuShangfeng Yangπ-Conjugation-extended dinaphthocarbazole phosphonic acid as a hole-selective layer for inverted perovskite solar cells. Acta Physico-Chimica Sinica, 2026, 42(3): 100194-0. doi: 10.1016/j.actphy.2025.100194

Metrics
  • PDF Downloads(4)
  • Abstract views(2215)
  • HTML views(326)

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