Citation: Wu Yuqin, Yu Liangyun, Zhang Qi, Li Lidong. Synthesis of Dihydrophenanthridines by Palladium-Catalyzed[2+2+2] Cyclization Reactions[J]. Chinese Journal of Organic Chemistry, ;2017, 37(9): 2336-2342. doi: 10.6023/cjoc201703004 shu

Synthesis of Dihydrophenanthridines by Palladium-Catalyzed[2+2+2] Cyclization Reactions

School of Chemistry and Chemical Engineering, Yancheng Institute of Technology, Yancheng 224051

Corresponding author: Li Lidong, ld-l@163.com
Received Date: 2 March 2017
Revised Date: 30 March 2017
Available Online: 10 September 2017
Fund Project: Project supported by the National Natural Science Foundation of China (No. 21272005)National Natural Science Foundation of China 21272005

Figures(3)

Phenanthridines are important core structures found in a variety of natural products and other biologically important molecules with a wide range of biological activities and applications, including antibacterial and anticancer agents. A practical and efficient domino method for the preparation of dihydrophenanthridines from diynes and aryl halides is developed via palladium-catalyzed[2+2+2] cycloaddition reactions. All new products were fully characterized by IR, ¹H NMR, ¹³C NMR and high-resolution mass spectrometry. The molecular structure of 1-(7, 12-diphenyl-5-tosyl-5, 6-dihydrobenzo[j]-phenanthridin-10-yl)ethan-1-one (3b) was confirmed by using single-crystal X-ray analyses.
- palladium-catalyzed,
- synthesis,
- C-C coupling,
- dihydrophenanthridine
1. [1]
  (a) Simeon, S.; Rios, J. L.; Villar, A. Pharmazie 1989, 44, 593.
  (b) Ishikawa, T.; Ishii, H. Heterocycles 1999, 50, 627.
2. [2]
  (a) Phillips, S. D.; Castle, R. N. J. Heterocycl. Chem. 1981, 18, 223.
  (b) Treus, M.; Estevez, J. C.; Castedo, L.; Esteves, R. J. Tetrahedron Lett. 2002, 43, 532.
3. [3]
  (a) Bernardo, P. H.; Wan, K.-F.; Sivaraman, T.; Xu, J.; Moore, F. K.; Hung, A. W.; Mok, H. Y. K.; Yu, V. C.; Chai, C. L. L. J. Med. Chem. 2008, 51, 6699.
  (b) Janin, Y. L.; Croisy, A.; Riou, J.-F.; Bisagni, E. J. Med. Chem. 1993, 36, 3686.
  (c) Kock, I.; Heber, D.; Weide, M.; Wolschendorf, U.; Clement, B. J. Med. Chem. 2005, 48, 2772.
  (d) Treus, M.; Estevez, J. C.; Castedo, L.; Esteves, R. J. Tetrahedron Lett. 2002, 43, 5323.
  (e) Nakanishi, T.; Suzuki, M. Org. Lett. 1999, 1, 985.
4. [4]
  Cappoen, D.; Claes, P.; Jacobs, J.; Anthonissen, R.; Mathys, V.; Verschaeve, L.; Huygen, K.; Kimpe, N. D. J. Med. Chem. 2014, 57, 2895. doi: 10.1021/jm401735w
5. [5]
  Czapar, A. E.; Zheng, Y.-R.; Riddell, I. A.; Shukla, S.; Awuah, S. G.; Lippard, S. J.; Steinmetz, N. F. ACS Nano 2016, 10, 4119. doi: 10.1021/acsnano.5b07360
6. [6]
  Jiang, H.; He, J.; Liu, T.; Yu, J.-Q. J. Am. Chem. Soc. 2016, 138, 2055. doi: 10.1021/jacs.5b13462
7. [7]
8. [8]
  (a) Clement, B.; Weide, M.; Wolschendorf, U.; Kock, I. Angew. Chem., Int. Ed. 2005, 44, 635.
  (b) Candito, D. A.; Lautens, M. Angew. Chem., Int. Ed. 2009, 48, 6713.
  (c) Guo, C.; Huang, K.; Wang, B.; Xie, L.; Xu, X. RSC Adv. 2013, 3, 17271.
  (d) Gu, J.-W.; Zhang, X. Org. Lett. 2015, 17, 5384.
9. [9]
  (a) Deb, I.; Yoshikai, N. Org. Lett. 2013, 15, 4254.
  (b) Tu, H.-Y.; Liu, Y.-R.; Chu, J.-J.; Hu, B.-L.; Zhang, X.-G. J. Org. Chem. 2014, 79, 9907.
  (c) Wang, G.; Chen, S.-Y.; Yu, X.-Q. Tetrahedron Lett. 2014, 55, 5338.
  (d) Nie, Z.; Ding, Q.; Peng, Y. Tetrahedron, 2016, 72, 8350.
10. [10]
  Zhang, L.; Ang, G. Y.; Chiba, S. Org. Lett. 2010, 12, 3682. doi: 10.1021/ol101490n
11. [11]
  (a) Fang, H.; Zhao, J.; Ni, S.; Mei, H.; Han, J.; Pan, Y. J. Org. Chem. 2015, 80, 3151.
  (b) Lu, S.; Gong, Y.; Zhou, D. J. Org. Chem. 2015, 80, 9336.
  (c) Zhou, Y.; Wu, C.; Dong, X.; Qu, J. J. Org. Chem. 2016, 81, 5202.
  (d) Xiao, P.; Jian, Rong.; Ni, C.; Guo, J.; Li, X.; Chen, D.; Hu, J. Org. Lett. 2016, 18, 5912.
12. [12]
  (a) Linsenmeier, A. M.; Williams, C. M.; Bräse, S. J. Org. Chem. 2011, 76, 9127.
  (b) Zhang, Z.; Tang, X.; Dolbier, W. R., Jr. Org. Lett. 2015, 17, 4401.
  (c) Cheng, P.; Qing, Z.; Liu, S.; Liu, W.; Xie, H.; Zeng, J. Tetrahedron Lett. 2014, 55, 6647.
13. [13]
  (a) Read, M. L.; Gundersen, L.-L. J. Org. Chem. 2013, 78, 1311.
  (b) Xu, Y.; Chen, Y.; Li, W.; Xie, Q.; Shao, L. J. Org. Chem. 2016, 81, 8426.
14. [14]
  Mehta, B. K.; Yanagisawa, K.; Shiro, M.; Kotsuki, H. Org. Lett. 2003, 5, 1605. doi: 10.1021/ol0300120
15. [15]
  Tummatorn, J.; Krajangsri, S.; Norseeda, K.; Thongsornkleeb, C.; Ruchirawat, S. Org. Biomol. Chem. 2014, 45, 5077.
16. [16]
  (a) Bras, J. L.; Muzart, J. Chem. Rev. 2011, 111, 1170.
  (b) Platon, M.; Amardeil, R.; Djakovitch, L.; Hierso, J.-C. Chem. Soc. Rev. 2012, 41, 3929.
17. [17]
18. [18]
  Sripada, L.; Teske, A. J.; Deiters, A. Org. Biomol. Chem. 2008, 6, 263. doi: 10.1039/B716519F
19. [19]
  Li, Y.; Zhu, J.; Zhang, L.; Wu, Y.; Gong, Y. Chem. Eur. J. 2013, 19, 8294. doi: 10.1002/chem.v19.25
20. [20]
  (a) Bedford, R. B.; Betham, M. J. Org. Chem. 2006, 71, 9403.
  (b) Gandeepan, P.; Parthasarathy, K.; Cheng, C.-H. J. Am. Chem. Soc. 2010, 132, 8569.
21. [21]
  (a) Hu, Y.; Ren, D.; Zhang, L.; Lin, X.; Wan J. Eur. J. Org. Chem. 2010, 23, 4454.
  (b) Hu, Y.; Yao, H.; Sun, Y.; Wan, J.; Lin, X, ; Zhu, T. Chem. Eur. J. 2010, 16, 7635.
22. [22]
  (a) Garca-Cuadrado, D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2006, 128, 1066.
  (b) Garca-Cuadrado, D.; Mendoza, P. D.; Braga, A. A. C.; Maseras, F.; Echavarren, A. M. J. Am. Chem. Soc. 2007, 129, 6880.
1. [1]
  Jiaming Xu , Yu Xiang , Weisheng Lin , Zhiwei Miao . Research Progress in the Synthesis of Cyclic Organic Compounds Using Bimetallic Relay Catalytic Strategies. University Chemistry, 2024, 39(3): 239-257. doi: 10.3866/PKU.DXHX202309093
2. [2]
  Jing WU , Puzhen HUI , Huilin ZHENG , Pingchuan YUAN , Chunfei WANG , Hui WANG , Xiaoxia GU . Synthesis, crystal structures, and antitumor activities of transition metal complexes incorporating a naphthol-aldehyde Schiff base ligand. Chinese Journal of Inorganic Chemistry, 2024, 40(12): 2422-2428. doi: 10.11862/CJIC.20240278
3. [3]
  Xinting XIONG , Zhiqiang XIONG , Panlei XIAO , Xuliang NIE , Xiuying SONG , Xiuguang YI . Synthesis, crystal structures, Hirshfeld surface analysis, and antifungal activity of two complexes Na(Ⅰ)/Cd(Ⅱ) assembled by 5-bromo-2-hydroxybenzoic acid ligands. Chinese Journal of Inorganic Chemistry, 2024, 40(9): 1661-1670. doi: 10.11862/CJIC.20240145
4. [4]
  Renxiao Liang , Zhe Zhong , Zhangling Jin , Lijuan Shi , Yixia Jia . A Palladium/Chiral Phosphoric Acid Relay Catalysis for the One-Pot Three-Step Synthesis of Chiral Tetrahydroquinoline. University Chemistry, 2024, 39(5): 209-217. doi: 10.3866/PKU.DXHX202311024
5. [5]
  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
6. [6]
  Wenjiang LI , Pingli GUAN , Rui YU , Yuansheng CHENG , Xianwen WEI . C₆₀-MoP-C nanoflowers van der Waals heterojunctions and its electrocatalytic hydrogen evolution performance. Chinese Journal of Inorganic Chemistry, 2024, 40(4): 771-781. doi: 10.11862/CJIC.20230289
7. [7]
  Wei Zhong , Dan Zheng , Yuanxin Ou , Aiyun Meng , Yaorong Su . K原子掺杂高度面间结晶的g-C₃N₄光催化剂及其高效H₂O₂光合成. Acta Physico-Chimica Sinica, 2024, 40(11): 2406005-. doi: 10.3866/PKU.WHXB202406005
8. [8]
  Guoqiang Chen , Zixuan Zheng , Wei Zhong , Guohong Wang , Xinhe Wu . 熔融中间体运输导向合成富氨基g-C₃N₄纳米片用于高效光催化产H₂O₂. Acta Physico-Chimica Sinica, 2024, 40(11): 2406021-. doi: 10.3866/PKU.WHXB202406021
9. [9]
  Lili Jiang , Shaoyu Zheng , Xuejiao Liu , Xiaomin Xie . Copper-Catalyzed Oxidative Coupling Reactions for the Synthesis of Aryl Sulfones: A Fundamental and Exploratory Experiment for Undergraduate Teaching. University Chemistry, 2025, 40(7): 267-276. doi: 10.12461/PKU.DXHX202408004
10. [10]
  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
11. [11]
  Xi YANG , Chunxiang CHANG , Yingpeng XIE , Yang LI , Yuhui CHEN , Borao WANG , Ludong YI , Zhonghao HAN . Co-catalyst Ni₃N supported Al-doped SrTiO₃: Synthesis and application to hydrogen evolution from photocatalytic water splitting. Chinese Journal of Inorganic Chemistry, 2025, 41(3): 440-452. doi: 10.11862/CJIC.20240371
12. [12]
  Lewang Yuan , Yaoyao Peng , Zong-Jie Guan , Yu Fang . 二维共价有机框架作为光催化剂在有机合成中的研究进展. Acta Physico-Chimica Sinica, 2025, 41(8): 100086-. doi: 10.1016/j.actphy.2025.100086
13. [13]
  Qinghong Zhang , Qiao Zhao , Xiaodi Wu , Li Wang , Kairui Shen , Yuchen Hua , Cheng Gao , Yu Zhang , Mei Peng , Kai Zhao . Visible-light-induced ring-opening cross-coupling of cycloalcohols with vinylazaarenes and enones via β-C-C scission enabled by proton-coupled electron transfer. Chinese Chemical Letters, 2025, 36(2): 110167-. doi: 10.1016/j.cclet.2024.110167
14. [14]
  Minna Ma , Yujin Ouyang , Yuan Wu , Mingwei Yuan , Lijuan Yang . Green Synthesis of Medical Chemiluminescence Reagents by Photocatalytic Oxidation. University Chemistry, 2024, 39(5): 134-143. doi: 10.3866/PKU.DXHX202310093
15. [15]
  Qin Li , Huihui Zhang , Huajun Gu , Yuanyuan Cui , Ruihua Gao , Wei-Lin Dai . In situ Growth of Cd_0.5Zn_0.5S Nanorods on Ti₃C₂ MXene Nanosheet for Efficient Visible-Light-Driven Photocatalytic Hydrogen Evolution. Acta Physico-Chimica Sinica, 2025, 41(4): 100031-. doi: 10.3866/PKU.WHXB202402016
16. [16]
  Jianyu Qin , Yuejiao An , Yanfeng Zhang . In Situ Assembled ZnWO₄/g-C₃N₄ S-Scheme Heterojunction with Nitrogen Defect for CO₂ Photoreduction. Acta Physico-Chimica Sinica, 2024, 40(12): 2408002-. doi: 10.3866/PKU.WHXB202408002
17. [17]
  Zhiwen HU , Weixia DONG , Qifu BAO , Ping LI . Low-temperature synthesis of tetragonal BaTiO₃ for piezocatalysis. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 857-866. doi: 10.11862/CJIC.20230462
18. [18]
  Guimin ZHANG , Wenjuan MA , Wenqiang DING , Zhengyi FU . Synthesis and catalytic properties of hollow AgPd bimetallic nanospheres. Chinese Journal of Inorganic Chemistry, 2024, 40(5): 963-971. doi: 10.11862/CJIC.20230293
19. [19]
  Shihui Shi , Haoyu Li , Shaojie Han , Yifan Yao , Siqi Liu . Regioselectively Synthesis of Halogenated Arenes via Self-Assembly and Synergistic Catalysis Strategy. University Chemistry, 2024, 39(5): 336-344. doi: 10.3866/PKU.DXHX202312002
20. [20]
  Chi Li , Jichao Wan , Qiyu Long , Hui Lv , Ying Xiong . N-Heterocyclic Carbene (NHC)-Catalyzed Amidation of Aldehydes with Nitroso Compounds. University Chemistry, 2024, 39(5): 388-395. doi: 10.3866/PKU.DXHX202312016

Get Citation

PDF

XML

Metrics

PDF Downloads(3)
Abstract views(2068)
HTML views(935)

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