Citation: Dong Kun, Li Qiuyun, An Kang, Ma Junyi, Bai Zhongsheng, Liu Qiancai. Palladium-Catalyzed Syntheses of C₃-Symmetric 9-Aryl Acridine Derivatives[J]. Chinese Journal of Organic Chemistry, ;2018, 38(2): 416-424. doi: 10.6023/cjoc201707007 shu

Palladium-Catalyzed Syntheses of C₃-Symmetric 9-Aryl Acridine Derivatives

School of Chemistry and Molecular and Engineering, East China Normal University, Shanghai 200241

Corresponding author: Liu Qiancai, 9cliu@chem.ecnu.edu.cn
Received Date: 6 July 2017
Revised Date: 23 September 2017
Available Online: 11 February 2017

Figures(7)

A multiple synthetic strategy is employed to furnish the synthesis of 6, 12, 18-triaryldibenzo[b, j]quinoline[2, 3-f] [1, 7]phenanthroline. The key intermediate 6, 12, 18-trichlorobenzotriquinoline was prepared by Buchwald-Hartwig reaction of 1, 3, 5-tribromobenzene with methyl anthranilate, followed by hydrolysis and POCl₃-promoted ring closure reaction. The palladium-catalyzed Suzuki coupling was carried out with a novel catalyst Pd-132 to form fourteen C₃-symmetric 9-aryl acridine derivatives. The reactions can be performed at low catalyst loading (0.1 mol%, ca. 0.03 mol% per site).
- Buchwald-Hartwig reaction,
- acridine,
- Pd-132,
- Suzuki coupling
1. [1]
  (a) Feng, X. ; Wu, J. ; Ai, M. ; Pisula, W. ; Zhi, L. ; Rabe, J. P. ; Mllen, K. Angew. Chem., Int. Ed. 2007, 46, 3033.
  (b) Piot, L. ; Marie, C. ; Feng, X. L. ; Müllen, K. ; Fichou, D. Adv. Mater. 2008, 20, 3854.
  (c) Simpson, C. D. ; Wu, J. S. ; Watson, M. D. ; Mullen, K. J. Mater. Chem. 2004, 14, 494.
  (d) Bertrand, H. ; Guillot, R. ; Teulade-Fichou, M. -P. ; Fichou, D. Chem. -Eur. J. 2013, 19, 14654.
  (e) Piot, L. ; Marie, C. ; Dou, X. ; Feng, X. L. ; Mullen, K. ; Fichou, D. J. Am. Chem. Soc. 2009, 131, 1378.
2. [2]
  Rüdiger, E. C.; Rominger, F.; Steuer, L.; Bunz. U. H. F. J. Org. Chem. 2016, 81, 193. doi: 10.1021/acs.joc.5b02481
3. [3]
4. [4]
  Goodell, J. R.; Ougolkov, A. V.; Hiasa, H.; Kaur, H.; Remmel, R.; Billadeau, D. D.; Ferguson, D. M. J. Med. Chem. 2008, 51, 179. doi: 10.1021/jm701228e
5. [5]
  Horowitz, E. D.; Hud, N. V. J. Am. Chem. Soc. 2006, 128, 15380. doi: 10.1021/ja065339l
6. [6]
  Hassan, S.; Laryea, D.; Mahteme, H.; Felth, J.; Fryknäs, M.; Fayad, W.; Linder, S.; Rickardson, L.; Gullbo, J.; Graf, W.; Påhlman, L.; Glimelius, B.; Larsson R.; Nygren, P. Cancer Sci. 2011, 102, 2206. doi: 10.1111/cas.2011.102.issue-12
7. [7]
  Ephrussi, B.; Hottinguer, H. Nature 1950, 166, 956.
8. [8]
  Musdal, Y.; Hegazy, U. M.; Aksoy Y.; Mannervik, B. Chem. Biol. Interact. 2013, 205, 53. doi: 10.1016/j.cbi.2013.06.003
9. [9]
  Mei, Q.; Li, X. L.; Liu, H. J.; Zhou, H. B. Eur. J. Obstet. Gynecol. Reprod. Biol. 2014, 178, 12. doi: 10.1016/j.ejogrb.2014.04.041
10. [10]
  Kumar, R.; Kaur M.; Kumari, M. Acta Pol. Pharm. 2012, 69, 3.
11. [11]
  Galdino-Pitta, M. R.; Pitta, M. G. R.; Lima, M. C. A.; Galdino S. L.; Pitta, I. R. Mini-Rev. Med. Chem. 2013, 13, 1256. doi: 10.2174/1389557511313090002
12. [12]
  Cain, B. F.; Atwell, G. J.; Denny, W. A. J. Med. Chem. 1975, 18, 1110. doi: 10.1021/jm00245a013
13. [13]
  Atwell, G. J.; Rewcastle, G. W.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1987, 30, 664. doi: 10.1021/jm00387a014
14. [14]
  Spicer, J. A.; Gamage, S. A.; Atwell, G. J.; Finlay, G. J.; Baguley, B. C.; Denny, W. A. J. Med. Chem. 1997, 40, 1919. doi: 10.1021/jm970004n
15. [15]
  Gamage, S. A.; Spicer, J. A.; Rewcastle G. W.; Denny, W. A. Tetrahedron Lett. 1997, 38, 699. doi: 10.1016/S0040-4039(96)02396-9
16. [16]
  Dittrich, C.; Dieras, V.; Kerbrat, P.; Punt, C.; Sorio, R.; Caponigro, F. Invest. New Drugs 2003, 21, 347. doi: 10.1023/A:1025476813365
17. [17]
  Kestemont, G.; de Halleux, V.; Lehmann, M.; Ivanov, D. A.; Watson, M.; Geerts, Y. H. Chem. Commun. 2001, 2074.
18. [18]
  Ong, C. W.; Liao, S. C.; Chang, T. H.; Hsu, H. F. Tetrahedron Lett. 2003, 44, 1477. doi: 10.1016/S0040-4039(02)02862-9
19. [19]
  Lemaur, V.; Filho, D. A. S.; Coropceanu, V.; Lehmann, M.; Geerts, Y.; Piris, J.; Debije, M. G.; van de Craats, A. M.; Senthilkumar, K.; Siebbeles, L. D. A.; Warman, J. M.; Brdas, J. L.; Cornil, J. J. Am. Chem. Soc. 2004, 126, 3271. doi: 10.1021/ja0390956
20. [20]
  Qiu, F.; Zhang, F.; Tang, R. Z.; Fu, Y. B.; Wang, X. Y.; Han, S.; Zhuang, X. D.; Feng, X. L. Org. Lett. 2016, 18, 1398. doi: 10.1021/acs.orglett.6b00335
21. [21]
  (a) Gavathiotis, E. ; Heald, R. A. ; Stevens, M. F. G. ; Searle, M. S. J. Mol. Biol. 2003, 334, 25.
  (b) Bertrand, H. ; Granzhan, A. ; Monchaud, D. ; Saettel, N. ; Guillot, R. ; Clifford, S. ; Guedin, A. ; Mergny, J. L. ; Teulade-Fichou, M. P. Chem. -Eur. J. 2011, 17, 4529.
22. [22]
  Plater, M. J.; McKay, M.; Jackson, T. J. Chem. Soc., Perkin Trans. 1 2000, 2695.
23. [23]
  (a) Saettel, N. ; Katsonis, N. ; Marchenko, A. ; Teulade-Fichou, M. -P. ; Fichou, D. J. Mater. Chem. 2005, 15, 3175.
  (b) Jacquelin, C. ; Saettel, N. ; Hounsou, C. ; Teulade-Fichou, M. P. Tetrahedron Lett. 2005, 46, 2589.
24. [24]
  (a) Ge, H. M. ; Liu, Q. C. Heterocycles 2015, 91, 1001.
  (b) Ye, P. J. ; Li, Q. Y. ; Bai, Z. S. ; Dong, K. ; Liu, Q. C. Heterocycles 2015, 91, 1986.
  (c) Zhang, J. ; Ye, P. J. ; He, L. ; Yuan, T. ; Liu, Q. C. Heterocycles 2015, 91, 2190.
25. [25]
  Huang, C. H. ; Li, F. Y. ; Huang, W. Introduction to Organic Light-Emitting Materials and Devices, Fudan University Press, Shanghai, 2005, p. 110(in Chinese).
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Palladium-Catalyzed Syntheses of C₃-Symmetric 9-Aryl Acridine Derivatives