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

State Key Laboratory Breeding Base of Green Chemistry-Synthesis Technology, College of Chemical Engineering, Zhejiang University of Technology, Hangzhou 310014

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.
- phthaline diamine,
- alkyne,
- bifunctional phosphine ligand,
- gold catalysis,
- 1, 5-benzodiazepine
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
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 ZHU , Xufeng 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 LUO , Pintian ZOU , Xiaoyan WANG , Zheng LIU , Xiangfei KONG , Qun TANG , Sheng 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 ZHU , Xufeng 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 ZHANG , Yiwei SHI , Ruijie YANG , Xin WANG , Zhiguo SONG , Min 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]
  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
7. [7]
  Zhenhuan Wang , Weifei Wei , Ruijie Ma , Dou Luo , Zhanxiang Chen , Jun Zhang , Liyang Yu , Gang Li , Zhenghui 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
8. [8]
  Jichao XU , Ming HU , Xichang CHEN , Chunhui WANG , Leichen WANG , Lingyi ZHOU , Xing HE , Xiamin CHENG , Su 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
9. [9]
  Jie ZHAO , Sen LIU , Qikang YIN , Xiaoqing LU , Zhaojie 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]
  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
11. [11]
  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
12. [12]
  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
13. [13]
  Hong RAO , Yang HU , Yicong MA , Chunxin LÜ , Wei ZHONG , Lihua 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
14. [14]
  Yanglin Jiang , Mingqing Chen , Min Liang , Yige Yao , Yan Zhang , Peng Wang , Jianping 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
15. [15]
  Shantao Zhang , TianAo Hou , Yandong Wang , Zhimin Fang , Yu Wu , Haolin Wang , Tao Chen , Shuang Chen , Wenhua Zhang , Shengzhong (Frank) Liu , Shangfeng Yang . π-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
16. [16]
  Xiuyun Wang , Jiashuo Cheng , Yiming Wang , Haoyu Wu , Yan Su , Yuzhuo Gao , Xiaoyu Liu , Mingyu Zhao , Chunyan Wang , Miao Cui , Wenfeng Jiang . Improvement of Sodium Ferric Ethylenediaminetetraacetate (NaFeEDTA) Iron Supplement Preparation Experiment. University Chemistry, 2024, 39(2): 340-346. doi: 10.3866/PKU.DXHX202308067
17. [17]
  Lifang HE , Wenjie TANG , Yaoze LUO , Mingsheng LIANG , Jianxin TANG , Yuxuan WU , Fuxing ZHANG , Xiaoming ZHU . Synthesis, structure, and anticancer activity of two dialkyltin complexes constructed based on 2, 2′-bipyridin-6, 6′-dicarboxylic acid. Chinese Journal of Inorganic Chemistry, 2025, 41(8): 1601-1609. doi: 10.11862/CJIC.20250012
18. [18]
  Ruifeng CHEN , Chao XU , Jianting JIANG , Tianshe YANG . Gold nanorod/zinc oxide/mesoporous silica nanoplatform: A triple-modal platform for synergistic anticancer therapy. Chinese Journal of Inorganic Chemistry, 2025, 41(11): 2272-2282. doi: 10.11862/CJIC.20250117
19. [19]
  Xiyuan Zhang , Rui Dong , Yang Yang , Jiapeng Ding , Zhiwei Miao . Palladium-Catalyzed Tandem Cyclization of 4-Vinylbenzoxazinone and Indene-2-carbaldehyde: A Comprehensive Organic Chemistry Experiment. University Chemistry, 2025, 40(9): 361-367. doi: 10.12461/PKU.DXHX202410062
20. [20]
  Yue Zhao , Yanfei Li , Tao Xiong . Copper Hydride-Catalyzed Nucleophilic Additions of Unsaturated Hydrocarbons to Aldehydes and Ketones. University Chemistry, 2024, 39(4): 280-285. doi: 10.3866/PKU.DXHX202309001

Get Citation

PDF

XML

Metrics

PDF Downloads(4)
Abstract views(1835)
HTML views(277)

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