Chinese Journal of Organic Chemistry >
Selective Reduction of β-Keto Amides to α,β-Unsaturated Olefinic Amides and β-Hydroxy Amides by Using Sodium Borohydride as the Reductant
Received date: 2016-03-13
Revised date: 2016-03-29
Online published: 2016-04-15
Supported by
Project supported by the Excellent Youth Foundation of Guangdong Province (No. 2013LYM_0059).
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.
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
[1] Clemens, R. J. Chem. Rev. 1986, 86, 241.
[2] Nishiwaki, N.; Nakaike, Y.; Ariga, M. J. Oleo Sci. 2008, 57, 53.
[3] Han, M.; Nam, K. D.; Hahn, H. G..; Shin, D. Tetrahedron Lett. 2008, 49, 5217.
[4] Wang, Y.; Xin, X.; Liang, Y.; Lin, Y.; Duan, H.; Dong, D. Adv. Synth. Catal. 2009, 351, 2217.
[5] Tan, L. Q.; Zhou, P.; Chen, C.; Liu, W. B. Beilstein J. Org. Chem. 2013, 9, 2681.
[6] Wang, Z. K.; Bi, X. H.; Liao, P. Q.; Liu, X.; Dong, D. W. Chem. Commun. 2013, 49, 1309.
[7] Hu, Y. Q.; Fu, X. L.; Barry, B. D.; Bi, X. H.; Dong, D. W. Chem. Commun. 2012, 48, 690.
[8] Knapp, J. M.; Zhu, J. S.; Wood, A. B.; Kurth, M. J. ACS Comb. Sci. 2012, 14, 85.
[9] Zhang, Z. G..; Fang, S. L.; Liu, Q. F.; Zhang, G. S. J. Org. Chem. 2012, 77, 7665.
[10] Liu, W. B.; Chen, C.; Zhang, Q.; Zhu, Z. B. Beilstein J. Org. Chem. 2011, 7, 1436.
[11] Liu, W. B.; Chen, C.; Zhang, Q.; Zhu, Z. B. Beilstein J. Org. Chem. 2012, 8, 344.
[12] Zhang, Q.; Liu, W. B.; Chen, C.; Tan, L. Q. Chin. J. Chem. 2013, 31, 453.
[13] Liu, W. B.; Zhou, P.; Chen, C.; Zhang, Q.; Zhu. Z. B. Org. Biomol. Chem. 2013, 11, 542.
[14] Zhang, T. K.; Mo, D. L.; Dai, L. X.; Hou, X. L. Org. Lett. 2008, 10, 5337.
[15] Bartoli, G..; Bellucci, M. C.; Petrini, M.; Marcantoni, E.; Sambri, L.; Torregiani, E. Org. Lett. 2000, 2, 1791.
[16] Skoda, E. M.; Davis, G. C.; Wipf, P. Org. Process Res. Dev. 2012, 16, 26.
[17] Nishio, S.; Somete, T.; Sugie, A.; Kobayashi, T.; Yaita, T.; Mori, A. Org. Lett. 2012, 14, 2476.
[18] Jang, Y. J.; Yan, M. C.; Lin, Y. F.; Yao, C. F. J. Org. Chem. 2004, 69, 3961.
[19] Nishio, S.; Somete, T.; Sugie, A.; Kobayashi, T.; Yaita, T.; Mori, A. Org. Lett. 2012, 14, 2476.
[20] Jang, Y. J.; Yan, M. C.; Lin, Y. F.; Yao, C. F. J. Org. Chem. 2004, 69, 3961.
[21] Ma, Z. X.; Feltenberger, J. B.; Hsung, R. P. Org. Lett. 2012, 14, 2742.
[22] Forment?n, P.; Gimeno, N.; Steinke, I. H. G.; Vilar, R. J. Org. Chem. 2005, 70, 8235.
[23] Eriksson, J.; Åberg, O.; Långström, B. Eur. J. Org. Chem. 2007, 455.
[24] Xiong, T.; Li, Y.; Bi, H. X.; Lv, Y. H.; Zhang, Q. Angew. Chem., Int. Ed. 2011, 50, 7140.
[25] Curran, D. P.; Liu, W. D.; Chen, C. H. T. J. Am. Chem. Soc. 1999, 121, 11012.
[26] Merchant, J. R. Curr. Sci. 1979, 48, 13.
[27] Couture, L.; Mathieu, J. P. Compt. Rend. 1948, 226, 1261.
[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] Faraji, L.; Jadidi, K.; Notash, B. Tetrahedron Lett. 2014, 55, 346.
[30] Ryosuke, H.; Seijiro, M. Synthesis 2014, 46, 2272.
[31] Yosuke, D.; Yuki, K.; Yoshihiro, M.; Osamu, O. Synlett 2008, 433.
[32] Kawashima, E.; Takada, T.; Tabei, K. J. Heterocycl. Chem. 1985, 22, 1409.
/
| 〈 |
|
〉 |
