Citation: Feng Chunlai, Zhu Jie, Tang Qiujie, Zhou Aihua. Synthesis of ArSe-Substituted Flavone Derivatives Using Se Powder[J]. Chinese Journal of Organic Chemistry, ;2019, 39(4): 1187-1192. doi: 10.6023/cjoc201808011 shu

Synthesis of ArSe-Substituted Flavone Derivatives Using Se Powder

Pharmacy School, Jiangsu University, Zhenjiang 212013

Corresponding author: Zhou Aihua, ahz@ujs.edn.cn
Received Date: 10 August 2018
Revised Date: 20 September 2018
Available Online: 11 April 2018
Fund Project: Jiangsu University 1281290006Project supported by Jiangsu University (No. 1281290006)

Figures(2)

New flavone derivatives are highly valued in drug discovery due to their diversity of important bioactivities. Herein, one simple Cu-catalyzed method of constructing C-Se bonds on flavone structures using convenient Se powder via C-H functionalization is reported, regioselectively affording ArSe-substituted flavone derivatives in good yields.
- selenium,
- C—Se bond,
- flavone,
- selenide,
- C—H functionalization
1. [1]
  (a) Espargaro, A.; Ginex, T.; Vadell, M. D.; Busquets, M. A.; Estelrich, J.; Munoz-Torrero, D.; Luque, F. J.; Sabate, R. J. Nat. Prod. 2017, 80, 278.
  (b) Tsou, L. K.; Lara-Tejero, M.; RoseFigura, J.; Zhang, Z. J.; Wang, Y. C.; Yount, J. S.; Lefebre, M.; Dossa, P. D.; Kato, J.; Guan, F.; Lam, W.; Cheng, Y. C.; Galan, J. E.; Hang, H. C. J. Am. Chem. Soc. 2016, 138, 2209.
  (c) Cragg, G. M.; Grothaus, P. G.; Newman, D. J. Chem. Rev. 2009, 109, 3012.
2. [2]
  (a) Chen, H.; Olatunji, O. J.; Zhou, Y. J. Nat. Med. 2016, 70, 610.
  (b) Zhou, Z.; Tang, M.; Liu, Y.; Zhang, Z.; Lu, R.; Lu, J. Anti-Cancer Drugs 2017, 28, 446.
  (c) Gaspar, A.; Matos, M. J.; Garrido, J.; Uriarte, E.; Borges, F. Chem. Rev. 2014, 114, 4960.
3. [3]
  (a) Kim, Y.-W.; Hackett, J. C.; Brueggemeier, R. W. J. Med. Chem. 2004, 47, 4032.
  (b) Francisco, V.; Figueirinha, A.; Costa, G.; Liberal, J.; Ferreira, I.; Lopes, M. C.; García-Rodríguez, C.; Cruz, M. T.; Batista, M. T. J. Nat. Prod. 2016, 79, 1423.
  (c) Wang, Q.; Du, X.; Zhou, B.; Li, J.; Lu, W.; Chen, Q.; Gao, J. Biomed. Pharmacother. 2017, 96, 396.
  (d) Van Acker A. A. F.; Hageman, A. J.; Haenen R. M. M. G.; Van der Vijgh J. F. W.; Bast, A.; Menge, M. P. B. W. J. Med. Chem. 2000, 43, 3752.
  (e) Lin, S.; Koh, J.-J.; Aung, T. T.; Ling, W.; Sin, W.; Lim, F.; Wang, L.; Lakshminarayanan, R.; Zhou, L.; Tan, D.; Cao, D.; Beuerman, R. W.; Ren, L.; Liu S. J. Med. Chem. 2017, 60, 6152.
  (f) Ribeiro, A.; Piló-Veloso, D.; Romanha, A. J.; Carlos, L.; Zani, C. J. Nat. Prod. 1997, 60, 836.
4. [4]
5. [5]
  (a) Shirizi, A. N.; Tiwari, R.; Oh, D.; Sullivan, S.; Kumar, A.; Beni, Y.; Parang, K. Mol. Pharmaceutics 2014, 11, 3631.
  (b) Cao, S.; Durrani, F. A.; Rustum, Y. M. Clin. Cancer Res. 2004, 10, 2561.
  (c) Madhunapantula, S. V.; Desai, D.; Sharma, A.; Huh, S. J.; Amin, S.; Robertson, G. P. Mol. Cancer. Ther. 2008, 7, 1297.
  (d) Liu, M.; Li, Y.; Yu, L.; Xu, Q.; Jiang, X. Sci. China, Chem. 2018, 61, 294.
  (e) Yu, L.; Wu, Y.; Chen, T.; Pan, Y.; Xu, Q. Org. Lett. 2013, 15, 144.
  (f) Jing, X.; Yuan, D.; Yu, L. Adv. Synth. Catal. 2017, 359, 1194.
  (g) Wang, Y.; Yu, L.; Zhu, B.; Yu, L. J. Mater. Chem. A 2016, 4, 10828.
  (h) Yu, L.; Chen, F.; Ding, Y. ChemCatChem 2016, 8, 1033.
  (i) Yu, L.; Li, H.; Zhang, X.; Ye, J.; Liu, J.; Xu, Q.; Lautens, M. Org. Lett. 2014, 16, 1346.
6. [6]
  (a) Zhao, W. N.; Xie, P.; Bian, Z. G.; Zhou, A. H.; Ge, H.; Zhang, M.; Ding, Y.; Zheng, L. J. Org. Chem. 2015, 80, 9167.
  (b) Niu, B.; Zhao, W. N.; Ding, Y. C.; Bian, Z.; Pittman, C. U. Jr.; Zhou, A. H.; Ge, H. J. Org. Chem. 2015, 80, 7251.
  (c) Yatabe, T.; Jin, X.; Mizuno, N.; Yamaguchi, K. ACS Catal. 2018, 8, 4969.
  (d) Zhao, X.; Zhou, J.; Lin, S.; Jin, X.; Liu, R. Org. Lett. 2017, 19, 976.
  (e) Yang, Y. Q. Nat. Prod. Res. 2016, 30, 1628.
7. [7]
8. [8]
  (a) Zhao, W. N.; Xie, P.; Bian, Z. G.; Zhou, A. H.; Ge, H.; Niu, B.; Ding, Y. C. RSC Adv. 2015, 5, 59861.
  (b) Shi, L.-F.; Zhang, X.-G.; Zhang, X.-H. Tetrahedron 2016, 72, 8617.
9. [9]
10. [10]
  (a) Rafique, J.; Saba, S.; Schneider, A. R.; Franco, M. S.; Silva, S. M.; Braga, A. L. ACS Omega 2017, 2, 2280.
  (b) Zhong, S.; Liu, Y.; Cao, X.; Wan, J.-P. ChemCatChem 2017, 9, 465.
  (c) Benhur, G.; Adriane, S.; Bruning, C. A.; Back, D. F.; Henrique, M., P.; Nogueira, C. W.; Zeni, G. Adv. Synth. Catal. 2011, 353, 2042.
11. [11]
  (a) Min, L.; Wu, G.; Liu, M.; Gao, W.; Ding, J.; Chen, J.; Huang, X.; Wu, H. J. Org. Chem. 2016, 81, 7584.
  (b) Gao, C.; Wu, G.; Min, L.; Liu, M.; Gao, W.; Ding, J.; Chen, J.; Huang, X.; Wu, H. J. Org. Chem. 2017, 82, 250.
12. [12]
  Tang, Q.; Bian, Z.; Wu, W.; Wang, J.; Xie, P.; Pittman, C. U., Jr.; Zhou, A. J. Org. Chem. 2017, 82, 10617. doi: 10.1021/acs.joc.7b01320
13. [13]
  (a) Stubbing, L.; Li, F.; Furkert, D.; Caprio, V.; Brimble, M. Tetrahedron 2012, 68, 6948.
  (b) Yang, Y.; Qi, X.; Liu, R.; He, Q.; Yang, C. RSC Adv. 2016, 6, 103895.
  (c) Jaen, J.; Wise, L.; Heffner, T.; Pugsley, T.; Meltzer, L. J. Med. Chem. 1991, 34, 248.
  (d) He, Q.; So, C.; Bian, Z.; Hayashi, T.; Wang, J. Chem.-Asian J. 2015, 10, 540.
14. [14]
  Ding, Y. C.; Wu, W.; Zhao, W. N.; Li, Y.; Xie, P.; Huang, Y.; Liu, Y.; Zhou, A. H. Org. Biomol. Chem. 2016, 14, 1428. doi: 10.1039/C5OB02073E
15. [15]
  (a) Mohan, B.; Hwang, S.; Woo, H.; Park, K. H. Tetrahedron 2014, 70, 2699.
  (b) Soleiman-Beiji, M.; Yavari, I.; Sadeghizadeh, F. RSC Adv. 2015, 5, 87564.
  (c) Li, Z.; Ke, F.; Deng, H.; Xu, H.; Xiang, H.; Zhou, X. Org. Biomol. Chem. 2013, 11, 2943.
  (d) Singh, D.; Deobald, A. M.; Camargo, L. S.; Tabarelli, G.; Rodrigues, O. D.; Braga, A. Org. Lett. 2010, 12, 3288.
  (e) Guo, T. Synth. Commun. 2017, 47, 2053.
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