Citation: Li Jianxiao, Lin Shao, Huang Ruikang, Li Can, Yang Shaorong. Palladium-Catalyzed Cascade Cyclization/Bromination of 2-Alkynone O-Methyl Oximes in Ionic Liquid[J]. Chinese Journal of Organic Chemistry, ;2019, 39(5): 1417-1423. doi: 10.6023/cjoc201812006 shu

Palladium-Catalyzed Cascade Cyclization/Bromination of 2-Alkynone O-Methyl Oximes in Ionic Liquid

Li Jianxiao ^a,, ,
Lin Shao ^a ,
Huang Ruikang ^a ,
Li Can ^a ,
Yang Shaorong ^a,,

a.
School of Chemistry and Chemical Engineering, South China University of Technology, Guangzhou 510640

Corresponding author: Li Jianxiao, cejxli@scut.edu.cn Yang Shaorong, lisryang@scut.edu.cn
Received Date: 4 December 2018
Revised Date: 1 January 2019
Available Online: 18 May 2019
Fund Project: the National Natural Science Foundation of China 21502055the National Training Program of Innovation and Entrepreneurship for Undergraduates 201810561075the Fundamental Research Funds for the Central Universities 2018ZD16the National Natural Science Foundation of China 21642005Project supported by the National Natural Science Foundation of China (Nos. 21502055, 21642005), the Fundamental Research Funds for the Central Universities (No. 2018ZD16) and the National Training Program of Innovation and Entrepreneurship for Undergraduates (No. 201810561075)

Figures(2)

An efficient palladium-catalyzed protocol for the synthesis of 4-bromoisoxazoles derivatives in moderate to good yields from readily available O-methyl oximes in basic ionic liquid has been developed. Their structures were confirmed by ¹H NMR, ¹³C NMR and HRMS. This cascade cyclization/bromination process provides a novel route for directly accessing 4-bromoisoxazole in good to excellent yields and good functional group tolerance with high atom efficiency. Notably, the current methodology could also be conveniently applied to the synthesis of isoxazoles naturally occurring biologically active frameworks.
- ionic liquid,
- palladium catalysis,
- 2-alkynone O-methyloxime,
- 4-bromoisoxazole
1. [1]
  Pinhoe Melo, T. M. V. D. Curr. Org. Chem. 2005, 9, 925. doi: 10.2174/1385272054368420
2. [2]
  (a) Baraldi, P. G.; Barco, A.; Benetti, S.; Pollini, G. P.; Simon, D. Synthesis 1987, 857.
  (b) Heasley, B. Angew. Chem., Int. Ed. 2011, 50, 8474.
3. [3]
  Talley, J. J.; Brown, D. L.; Carter, J. S.; Graneto, M. J.; Koboldt, C. M.; Masferrer, J. L.; Perkins, W. E.; Rogers, R. S.; Shaffer, A. F.; Zhang, Y. Y.; Zweifel, B. S.; Seibert, K. J. Med. Chem. 2000, 43, 775. doi: 10.1021/jm990577v
4. [4]
  Dougados, M.; Emery, P.; Lemmel, E. M.; Zerbini, C. A.; Brin, F. S.; van Rie, P. Ann. Rheum. Dis. 2005, 64, 44. doi: 10.1136/ard.2003.016709
5. [5]
  Dong, K.-Y.; Qin, H.-T.; Bao, X.-X.; Liu, F.; Zhu, C. Org. Lett. 2014, 16, 5266. doi: 10.1021/ol502246t
6. [6]
  (a) Heaney, F. Eur. J. Org. Chem. 2012, 3043.
  (b) Gulevich, A. V.; Dudnik, A. S.; Chernyak, N.; Gevorgyan, V. Chem. Rev. 2013, 113, 3084.
7. [7]
  (a) Hu, F.; Szostak, M. Adv. Synth. Catal. 2015, 357, 2583.
  (b) Sperança, A.; Godoi, B.; Zeni, G. J. Org. Chem. 2013, 78, 1630.
8. [8]
  Tang, S.; He, J.; Sun, Y.; He, L.; She, X. J. Org. Chem. 2010, 75, 1961. doi: 10.1021/jo1000065
9. [9]
  Rossi, R.; Bellina, F.; Lessi, M.; Manzini, C.; Perego, L. A. Synthesis 2014, 46, 2833. doi: 10.1055/s-00000084
10. [10]
  Morita, T.; Yugandar, S.; Fuse, S.; Nakamura, H. Tetrahedron Lett. 2018, 59, 1159. doi: 10.1016/j.tetlet.2018.02.020
11. [11]
  (a) Waldo, J. P.; Larock, R. C. Org. Lett. 2005, 7, 5203.
  (b) Waldo, J. P.; Larock, R. C. J. Org. Chem. 2007, 72, 9643.
12. [12]
  Okitsu, T.; Sato, K.; Potewar, T. M.; Wada, A. J. Org. Chem. 2011, 76, 3438. doi: 10.1021/jo200407b
13. [13]
  Kaewsri, W.; Thongsornkleeb, C.; Tummatorn, J.; Ruchirawat, S. RSC Adv. 2016, 6, 48666. doi: 10.1039/C6RA09396E
14. [14]
  Li, J.; Hu, M.; Li, C.; Li, C.; Li, J.; Wu, W.; Jiang, H. Adv. Synth. Catal. 2018, 360, 2707. doi: 10.1002/adsc.v360.14
15. [15]
16. [16]
  (a) Li, J.; Jiang, H. Pd-Catalyzed Heterocycle Synthesis in Ionic Liquids, Ed.: Wu, X.-F., World Scientific Publishing, Imperial College Press, 2016, Chapter 8, pp. 351~368.
  (b) Li, J.; Yang, S.; Wu, W.; Jiang, H. Eur. J. Org. Chem. 2018, 1284.
17. [17]
  Jeong, Y.; Kim, B.-I.; Lee, J. K.; Ryu, J.-S. J. Org. Chem. 2014, 79, 6444. doi: 10.1021/jo5008702
18. [18]
  Guo, Y.-J.; Tang, R.-Y.; Li, J.-H.; Zhong, P.; Zhang, X.-G. Adv. Synth. Catal. 2009, 351, 2615. doi: 10.1002/adsc.v351:16
19. [19]
  Wu, W.; Li, C.; Li, J.; Jiang, H. Org. Biomol. Chem. 2018, 16, 8495. doi: 10.1039/C8OB01799A
20. [20]
  Fall, Y.; Reynaud, C.; Doucet, H.; Santelli, M. Eur. J. Org. Chem. 2009, 4041.
21. [21]
  She, Z.; Niu, D.; Chen, L.; Gunawan, M. A.; Shanja, X.; Hersh, W. H.; Chen, Y. J. Org. Chem. 2012, 77, 3627. doi: 10.1021/jo300090k
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