Citation: Meng Tuanjie, Feng Cuilan, Liu Lantao, Wang Tao, Xu Kai, Zhao Wenxian. Palladium Catalyzed Oxidation of Ynamides Using Dimethyl Sulfoxide as Oxidant: A Facile Way to Synthesize α-Ketoamide Derivatives[J]. Chinese Journal of Organic Chemistry, ;2016, 36(6): 1382-1388. doi: 10.6023/cjoc201601003 shu

Palladium Catalyzed Oxidation of Ynamides Using Dimethyl Sulfoxide as Oxidant: A Facile Way to Synthesize α-Ketoamide Derivatives

1.
Engineering Laboratory of Henan Province for Green Synthesis of Medicine, College of Chemistry and Chemical Engineering, Shangqiu Normal University, Shangqiu 476000

Corresponding author: Liu Lantao, liult05@iccas.ac.cn Zhao Wenxian, zhwx2595126@163.com
Received Date: 3 January 2016
Revised Date: 4 February 2016

Fund Project: the Science and Technology Key Project of Henan Province No. 142102210635and the Program for University Key Young Teachers of Henan Province No. 2015GGJS-126Project supported by the National Natural Science Foundation of China Nos. U1204204, 21172139, 21202095

Figures(2)

A series of α-ketoamide derivatives were obtained from the palladium catalyzed oxidation of ynamides using cheap and readily available dimethyl sulfoxide as oxidant and solvent under room temperature. The structures of all products were characterized by ¹H NMR, ¹³C NMR, IR and HRMS. This protocol has some distinct advantages of mild conditions, simple work-up, readily available starting materials and fast reaction rate.
- dimethyl sulfoxide,
- ynamides,
- α-ketoamides,
- synthesis,
- oxidation
1. [1]
  Kher, S. S.; Penzo, M.; Fulle, S.; Finn, P. W.; Blackman, M. J.; Jirgensons, A. Bioorg. Med. Chem. Lett. 2014, 24, 4486.
2. [2]
  Korukonda, R.; Guan, N.; Dalton, J. T.; Liu, J.; Donkor, I. O. J. Med. Chem. 2006, 49, 5282. (b) Donkor, I. O.; Han, J.; Zheng, X. J. Med. Chem. 2004, 47, 72. (c) Yoo, Y. J.; Nam, D. H.; Jung, S. Y.; Jang, J. W.; Kim, H. J.; Jin, C.; Pae, A. N.; Lee, Y. S. Bioorg. Med. Chem. Lett. 2011, 21, 2850. (d) Ovat, A.; Li, Z. Z.; Hampton, C. Y.; Asress, S. A.; Fernández, F. M.; Glass, J. D.; Powers, J. C. J. Med. Chem. 2010, 53, 6326.
3. [3]
  Mandadapu, S. R.; Weerawarna, P. M.; Gunnam, M. R.; Alliston, K. R.; Lushington, G. H.; Kim, Y.; Chang, K.-O.; Groutas, W. C. Bioorg. Med. Chem. Lett. 2012, 22, 4820.
4. [4]
  Steuer, C.; Gege, C.; Fischl, W.; Heinonen, K. H.; Bartenschlager, R.; Klein, C. D. Bioorg. Med. Chem. 2011, 19, 4067.
5. [5]
  Chen, J.-C.; Uang, B.-J.; Lyu, P.-C.; Chang, J.-Y.; Liu, K.-J.; Kuo, C.-C.; Hsieh, H.-P.; Wang, H.-C.; Cheng, C.-S.; Chang, Y.-H.; Chang, M. D.-T.; Chang, W.-S. W.; Lin, C.-C. J. Med. Chem. 2010, 53, 4545.
6. [6]
  Chiou, A.; Markidis, T.; Constantinou-Kokotou, V.; Verger, R.; KoKotos, G. Org. Lett. 2000, 2, 347.
7. [7]
  Bennett, F.; Huang, Y.; Hendrata, S.; Lovey, R.; Bogen, S. L.; Pan, W.; Guo, Z.; Prongay, A.; Chen, K. X.; Arasappan, A.; Venkatraman, S.; Velazquez, F.; Nair, L.; Sannigrahi, M.; Tong, X.; Pichardo, J.; Cheng, K.-C.; Girijavallabhan, V. M.; Saksena, A. K.; Njoroge, F. G. Bioorg. Med. Chem. Lett. 2010, 20, 2617.
8. [8]
  Lin, C.; Kwong, A. D.; Perni, R. B. Infect. Disord.: Drug Targets 2006, 6, 3.
9. [9]
  Schnopp, C.; Remling, R.; Möhrenschlager, M.; Weigl, L.; Ring, J.; Abeck, D. J. Am. Acad. Dermtol. 2002, 46, 73.
10. [10]
  Stella, S.; Chadha, A. Catal. Today 2012, 198, 345. (b) Singh, R. P.; Shreeve, J. M. J. Org. Chem. 2003, 68, 6063. (c) Guin, S.; Rout, S. K.; Gogoi, A.; Ali, W.; Patel, B. K. Adv. Synth. Catal. 2014, 356, 2559. (d) Zhang, X.; Yang, W.; Wang, L. Org. Biomol. Chem. 2013, 11, 3649. (e) Wang, H.; Guo, L.-N.; Duan, X.-H. Org. Biomol. Chem. 2013, 11, 4573.
11. [11]
12. [12]
13. [13]
  Dutta, S.; Kotha, S. S.; Sekar, G. RSC Adv. 2015, 5, 47265.
14. [14]
  Du, B.; Jin, B.; Sun, P. Org. Biomol. Chem. 2014, 12, 4586.
15. [15]
  Zhang, C.; Zong, X.; Zhang, L.; Jiao, N. Org. Lett. 2012, 14, 3280. (b) Mupparapu, N.; Khan, S.; Battula, S.; Kushwaha, M.; Gupta, A. P.; Ahmed, Q. N.; Vishwakarma, R. A. Org. Lett. 2014, 16, 1152.
16. [16]
  Zhang, C.; Xu, Z.; Zhang, L.; Jiao, N. Angew. Chem., Int. Ed. 2011, 50, 11088.
17. [17]
18. [18]
  Xing, Q.; Shi, L.; Lang, R.; Xia, C.; Li, F. Chem. Commun. 2012, 48, 11023.
19. [19]
  Al-Rashid, Z. F.; Johnson, W. L.; Hsung, R. P.; Wei, Y.; Yao, P.-Y.; Liu, R.; Zhao, K. J. Org. Chem. 2008, 73, 8780.
20. [20]
  Huang, H.; He, G.; Zhu, X.; Jin, X.; Qiu, S.; Zhu, H. Eur. J. Org. Chem. 2014, 7174.
21. [21]
  Chikugo, T.; Yauchi, Y.; Ide, M.; Iwasawa, T. Tetrahedron 2014, 70, 3988.
22. [22]
  Xu, C.-F.; Xu, M.; Jia, Y.-X.; Li, C.-Y. Org. Lett. 2011, 13, 1556. (b) Wang, K.-B.; Ran, R.-Q.; Xiu, S.-D.; Li, C.-Y. Org. Lett. 2013, 15, 2374.
23. [23]
  Zuo, J.-F.; Huang, W.-S.; Li, L.; Xu, Z.; Zheng, Z.-J.; Yang, K.-F.; Xu, L.-W. RSC Adv. 2015, 5, 30389. (b) Liu, F.-L.; Chen, J.-R.; Zuo, Y.-Q.; Wei, Q.; Xiao, W.-J. Org. Lett. 2014, 16, 3768. (c) Le, H. V.; Ganem, B. Org. Lett. 2011, 13, 2584. (d) Vieira, A. A.; Azeredo, J. B.; Godoi, M.; Santi, C.; Júnior, E. N. S.; Braga, A. L. J. Org. Chem. 2015, 80, 2120. (e) Prasad, P. K.; Reddi, R. N.; Sudalai, A. Org. Lett. 2016, 18, 500.
24. [24]
  Gao, A.; Yang, F.; Li, J.; Wu, Y. Tetrahedron 2012, 68, 4950.
25. [25]
  Dekorver, K. A.; Hsung, R. P.; Song, W.-Z.; Wang, X.-N.; Walton, M. C. Org. Lett. 2012, 14, 3214. (b) Wang, X.-N.; Winston-Mcpherson, G. N.; Walton, M. C.; Zhang, Y.; Hsung, R. P.; Dekorver, K. A. J. Org. Chem. 2013, 78, 6233. (c) Dekorver, K. A.; Johnson, W. L.; Zhang, Y.; Hsung, R. P.; Dai, H.; Deng, J.; Lohse, A. G.; Zhang, Y.-S. J. Org. Chem. 2011, 76, 5092.
26. [26]
  Huang, H.; He, G.; Zhu, G.; Zhu, X.; Qiu, S.; Zhu, H. J. Org. Chem. 2015, 80, 3480. (b) Istrate, F. M.; Buzas, A. K.; Jurberg, I. D.; Odabachian, Y.; Gagosz, F. Org. Lett. 2008, 10, 925. (c) Lu, Z.; Cui, W.; Xia, S.; Bai, Y.; Luo, F.; Zhu, G. J. Org. Chem. 2012, 77, 9871. (d) Lu, Z.; Xu, X.; Yang, Z.; Kong, L.; Zhu, G. Tetrahedron Lett. 2012, 53, 3433. (e) Hashmi, A. S. K.; Salathé, R.; Frey, W. Synlett 2007, 1763.
27. [27]
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