Citation: Chen Cui, Xu Songsen, Liu Weibing. Selective Reduction of β-Keto Amides to α,β-Unsaturated Olefinic Amides and β-Hydroxy Amides by Using Sodium Borohydride as the Reductant[J]. Chinese Journal of Organic Chemistry, ;2016, 36(8): 1890-1894. doi: 10.6023/cjoc201603020 shu

Selective Reduction of β-Keto Amides to α,β-Unsaturated Olefinic Amides and β-Hydroxy Amides by Using Sodium Borohydride as the Reductant

1.
College of Chemical Engineering, Guangdong University of Petrochemical Technology, Maoming 525000

Corresponding author: Chen Cui, cc161002@gdupt.edu.cn
Received Date: 13 March 2016
Revised Date: 29 March 2016

Fund Project: Project supported by the Excellent Youth Foundation of Guangdong Province No. 2013LYM_0059

Figures(1)

This paper reports a simple method for the synthesis of α,β-unsaturated olefinic amides from β-keto amides in the presence of NaBH₄ and alkali. However, this reaction only leads to quantitatively reduction product of carbonyl compounds in the presence of NaBH₄ and FeCl₃. The structures of products were confirmed by ¹H NMR and ¹³C NMR spectra. In addition, a possible reaction mechanism was also proposed.
- β-keto amides,
- α,β-unsaturated olefinic amides,
- reduction of carbonyl,
- NaBH₄
1. [1]
  Clemens, R. J. Chem. Rev. 1986, 86, 241.
2. [2]
  Nishiwaki, N.; Nakaike, Y.; Ariga, M. J. Oleo Sci. 2008, 57, 53.
3. [3]
  Han, M.; Nam, K. D.; Hahn, H. G..; Shin, D. Tetrahedron Lett. 2008, 49, 5217.
4. [4]
  Wang, Y.; Xin, X.; Liang, Y.; Lin, Y.; Duan, H.; Dong, D. Adv. Synth. Catal. 2009, 351, 2217.
5. [5]
  Tan, L. Q.; Zhou, P.; Chen, C.; Liu, W. B. Beilstein J. Org. Chem. 2013, 9, 2681.
6. [6]
  Wang, Z. K.; Bi, X. H.; Liao, P. Q.; Liu, X.; Dong, D. W. Chem. Commun. 2013, 49, 1309.
7. [7]
  Hu, Y. Q.; Fu, X. L.; Barry, B. D.; Bi, X. H.; Dong, D. W. Chem. Commun. 2012, 48, 690.
8. [8]
  Knapp, J. M.; Zhu, J. S.; Wood, A. B.; Kurth, M. J. ACS Comb. Sci. 2012, 14, 85.
9. [9]
  Zhang, Z. G..; Fang, S. L.; Liu, Q. F.; Zhang, G. S. J. Org. Chem. 2012, 77, 7665.
10. [10]
  Liu, W. B.; Chen, C.; Zhang, Q.; Zhu, Z. B. Beilstein J. Org. Chem. 2011, 7, 1436.
11. [11]
  Liu, W. B.; Chen, C.; Zhang, Q.; Zhu, Z. B. Beilstein J. Org. Chem. 2012, 8, 344.
12. [12]
  Zhang, Q.; Liu, W. B.; Chen, C.; Tan, L. Q. Chin. J. Chem. 2013, 31, 453.
13. [13]
  Liu, W. B.; Zhou, P.; Chen, C.; Zhang, Q.; Zhu. Z. B. Org. Biomol. Chem. 2013, 11, 542.
14. [14]
  Zhang, T. K.; Mo, D. L.; Dai, L. X.; Hou, X. L. Org. Lett. 2008, 10, 5337.
15. [15]
  Bartoli, G..; Bellucci, M. C.; Petrini, M.; Marcantoni, E.; Sambri, L.; Torregiani, E. Org. Lett. 2000, 2, 1791.
16. [16]
  Skoda, E. M.; Davis, G. C.; Wipf, P. Org. Process Res. Dev. 2012, 16, 26.
17. [17]
  Nishio, S.; Somete, T.; Sugie, A.; Kobayashi, T.; Yaita, T.; Mori, A. Org. Lett. 2012, 14, 2476.
18. [18]
  Jang, Y. J.; Yan, M. C.; Lin, Y. F.; Yao, C. F. J. Org. Chem. 2004, 69, 3961.
19. [19]
  Nishio, S.; Somete, T.; Sugie, A.; Kobayashi, T.; Yaita, T.; Mori, A. Org. Lett. 2012, 14, 2476.
20. [20]
  Jang, Y. J.; Yan, M. C.; Lin, Y. F.; Yao, C. F. J. Org. Chem. 2004, 69, 3961.
21. [21]
  Ma, Z. X.; Feltenberger, J. B.; Hsung, R. P. Org. Lett. 2012, 14, 2742.
22. [22]
  Formentĺn, P.; Gimeno, N.; Steinke, I. H. G.; Vilar, R. J. Org. Chem. 2005, 70, 8235.
23. [23]
  Eriksson, J.; Åberg, O.; Långström, B. Eur. J. Org. Chem. 2007, 455.
24. [24]
  Xiong, T.; Li, Y.; Bi, H. X.; Lv, Y. H.; Zhang, Q. Angew. Chem., Int. Ed. 2011, 50, 7140.
25. [25]
  Curran, D. P.; Liu, W. D.; Chen, C. H. T. J. Am. Chem. Soc. 1999, 121, 11012.
26. [26]
  Merchant, J. R. Curr. Sci. 1979, 48, 13.
27. [27]
  Couture, L.; Mathieu, J. P. Compt. Rend. 1948, 226, 1261.
28. [28]
  Sandrock, D. L.; Jean-Gérard, L.; Chen, C. Y.; Dreher, S. D. L.; Molander G. A. J. Am. Chem. Soc. 2010, 132, 17108.
29. [29]
  Faraji, L.; Jadidi, K.; Notash, B. Tetrahedron Lett. 2014, 55, 346.
30. [30]
  Ryosuke, H.; Seijiro, M. Synthesis 2014, 46, 2272.
31. [31]
  Yosuke, D.; Yuki, K.; Yoshihiro, M.; Osamu, O. Synlett 2008, 433.
32. [32]
  Kawashima, E.; Takada, T.; Tabei, K. J. Heterocycl. Chem. 1985, 22, 1409.
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