Citation: Zhang Xuewen, Li Pengfei, Yuan Yu, Jia Xiaodong. Synthesis of Quinoline Derivatives Containing Lactone Structure Promoted by Radical Cation Salt[J]. Chinese Journal of Organic Chemistry, ;2018, 38(9): 2435-2442. doi: 10.6023/cjoc201804012 shu

Synthesis of Quinoline Derivatives Containing Lactone Structure Promoted by Radical Cation Salt

Zhang Xuewen ^a ,
Li Pengfei ^b ,
Yuan Yu ^a,, ,
Jia Xiaodong ^a,,

a.
School of Chemistry & Chemical Engineering, Yangzhou University, Yangzhou 225002
b.
College of Chemistry & Chemical Engineering, Northwest Normal University, Lanzhou 730070

Corresponding author: Yuan Yu, yyuan@yzu.edu.cn Jia Xiaodong, jiaxd1975@163.com
Received Date: 8 April 2018
Revised Date: 17 May 2018
Available Online: 1 September 2018
Fund Project: Project supported by the National Natural Science Foundation of China (Nos. 1362030, 21562038)the National Natural Science Foundation of China 21562038the National Natural Science Foundation of China 1362030

Figures(3)

Using aniline derivatives containing lactone structure and styrenes as the starting materials, a series of lactone substituted quinolines were constructed efficiently by oxidative Povarov reaction, promoted by radical cation salt. This reaction provides a new method to achieve the construction of functionalized quinoline skeletons. The mechanistic study reveales that the oxidation of the saturated C-H bond is mediated by free radical intermediate.
- radical cation salt,
- C-H activation,
- Povarov reaction,
- quinoline,
- lactone
1. [1]
  (a) Zheng, Q.; Wang, S.; Liu, W. Tetrahedron 2014, 70, 7686.
  (b) Leeson, P. D.; Baker, R.; Carling, R. W.; Curtis, N. R.; Moore, K. W.; Williams, B. J.; Foster, A. C.; Donald, A. E.; Kemp, J. A.; Marshall, G. R. J. Med. Chem. 1991, 34, 1243.
  (c) Manfredini, S.; Pavan, B.; Vertuani, S.; Scaglianti, M.; Compagnone, D.; Biondi, C.; Scatturin, A.; Tanganelli, S.; Ferraro, L.; Prasad, P.; Dalpiaz, A. J. Med. Chem. 2002, 45, 559.
  (d) Pearce, A. N.; Chia, E. W.; Berridge, M. V.; Clark, G. R.; Harper, J. L.; Larsen, L.; Maas, E. W.; Page, M. J.; Perry, N. B.; Webb, V. L.; Copp, B. R. J. Nat. Prod. 2007, 70, 936.
2. [2]
  LaMontagne, M. P.; Blumbergs, P.; Smith, D. C. J. Med. Chem. 1989, 32, 1728. doi: 10.1021/jm00128a010
3. [3]
  Elmore, S. W.; Coghlan, M. J.; Anderson, D. D.; Pratt, J. K.; Green, B. E.; Wang, A. X.; Stashko, M. A.; Lin, C. W.; Tyree, C. M.; Miner, J. N.; Jacobson, P. B.; Wilcox, D. M.; Lane, B. C. J. Med. Chem. 2001, 44, 4481.
4. [4]
  Narender, P.; Srinivas, U.; Ravinder, M.; Rao, B. A.; Ramesh, C.; Harakishore, K.; Gangadasu, B.; Murthy, U. S. N.; Jayathirtha Rao, V. Bioorg. Med. Chem. 2006, 14, 4600. doi: 10.1016/j.bmc.2006.02.020
5. [5]
  (a) Curran, A. C. W. J. Chem. Soc., Perkin Trans. 1 1976, 975.
  (b) Misani, F.; Bogert, M. T. J. Org. Chem. 1945, 10, 347.
  (c) Chan, B. K.; Ciufolini, M. A. J. Org. Chem. 2007, 72, 8489.
6. [6]
  (a) Sakai, N.; Aoki, D.; Hamajima, T.; Konakahara, T. Tetrahe-dron Lett. 2006, 47, 1261.
  (b) Wu, Y. C.; Liu, L.; Li, H. J.; Wang, D.; Chen, Y. J. J. Org. Chem. 2006, 71, 6592.
  (c) Denmark, S. E.; Venkatraman, S. J. Org. Chem. 2006, 71, 1668;
  (d) Eisch, J. J.; Dluzniewski, T. J. Org. Chem. 1989, 54, 1269.
7. [7]
  (a) Ryabukhin, S. V.; Naumchik, V. S.; Plaskon, A. S.; Grygorenko, O. O.; Tolmachev, A. A. J. Org. Chem. 2011, 76, 5774.
  (b) Luo, W.; Mu, Q.; Qiu, W.; Liu, T.; Yang, F.; Liu, X.; Tang, J. Tetrahedron 2011, 67, 7090.
  (c) Atechian, S.; Nock, N.; Norcross, R. D.; Ratni, H.; Thomas, A. W.; Verron, J.; Masciadri, R. Tetrahedron 2007, 63, 2811.
  (d) Wu, J.; Xia, H. G.; Gao, K. Org. Biomol. Chem. 2006, 4, 126.
8. [8]
  (a) Kouznetsov, V. V. Tetrahedron 2009, 65, 2721.
  (b) Ribelles, P.; Sridharan, V.; Villacampa, M.; Ramos, M. T.; Menéndez, J. C. Org. Biomol. Chem. 2013, 11, 569.
  (c) Chandrashekarappa, K. K. H.; Mahadevan, K. M.; Manjappa, K. B. Tetrahedron Lett. 2013, 54, 1368.
9. [9]
10. [10]
  Hou, W.; Jia, X. Chin. J. Org. Chem. 2018, 38, 999(in Chinese).
11. [11]
  (a) Jia, X.; Zhu, Y.; Yuan, Y.; Zhang, X.; Lü, S.; Zhang, L.; Luo, L. ACS Catal. 2016, 6, 6033.
  (b) Jia, X.; Peng, F.; Qing, C.; Huo, C.; Wang, X. Org. Lett. 2012, 14, 4030.
  (c) Liu, J.; Liu, F.; Zhu, Y.; Ma, X.; Jia, X. Org. Lett. 2015, 17, 1409.
  (d) Jia, X.; Wang, Y.; Peng, F.; Huo, C.; Yu, L.; Liu, J.; Wang, X. Adv. Synth. Catal. 2014, 356, 1210.
  (e) Lv, S.; Zhu, Y.; Ma, X.; Jia, X. Adv. Synth. Catal. 2016, 358, 1004.
  (f) Jia, X.; Wang, Y.; Peng, F.; Huo, C.; Yu, L.; Liu, J.; Wang, X. J. Org. Chem. 2013, 78, 9450.
  (g) Wang, Y.; Peng, F.; Liu, J.; Huo, C.; Wang, X.; Jia, X. J. Org. Chem. 2015, 80, 609.
12. [12]
  Fort, D. A.; Woltering, T. J.; Nettekoven, M.; Knust, H.; Bach, T. Chem. Commun. 2013, 49, 2989. doi: 10.1039/c3cc40757h
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