Notes

Synthesis of Multi-substituted 1,4-Dihydropyridine Derivatives from Acetoacetanilides

  • Chen Cui ,
  • Tan Liquan ,
  • Qiu Huihua
Expand
  • College of Chemcal Engineering, Guangdong University of Petrochemical Technology, Maoming 525000

Received date: 2014-03-07

  Revised date: 2014-04-02

  Online published: 2014-04-18

Supported by

Project supported by the Natural Science Foundation of Guangdong Province (No. S2012040007868).

Abstract

This paper reports a simple intermolecular condensation reaction for the synthesis of 1,4-dihydropyridine derivatives from acetoacetanilides using AcOH as the solvent and ammonium persulfate[(NH4)2S2O4] as the oxidant. The structures of products were confirmed by IR, 1H NMR, 13C NMR and HR-MS. In addition, a possible reaction mechanism was proposed.

Cite this article

Chen Cui , Tan Liquan , Qiu Huihua . Synthesis of Multi-substituted 1,4-Dihydropyridine Derivatives from Acetoacetanilides[J]. Chinese Journal of Organic Chemistry, 2014 , 34(8) : 1673 -1676 . DOI: 10.6023/cjoc201403016

References

[1] Tan, L. Q.; Zhou, P.; Chen, C.; Liu, W. B. Beilstein J. Org. Chem. 2013, 9, 2681.
[2] Liu, W. B.; Zhou, P.; Chen, C.; Zhang, Q.; Zhu. Z. B. Org. Biomol. Chem. 2013, 11, 542.
[3] Clemens, R. J. Chem. Rev. 1986, 86, 241.
[4] Nishiwaki, N.; Nakaike, Y.; Ariga, M. J. Oleo Sci. 2008, 57, 53.
[5] Han, M.; Nam, K. D.; Hahn, H. G.; Shin, D. Tetrahedron Lett. 2008, 49, 5217.
[6] Wang, Y.; Xin, X.; Liang, Y.; Lin, Y.; Duan, H.; Dong, D. Adv. Synth. Catal. 2009, 351, 2217.
[7] Wang, Z. K.; Bi, X. H.; Liao, P. Q.; Liu, X.; Dong, D. W. Chem. Commun. 2013, 49, 1309.
[8] Hu, Y. Q.; Fu, X. L.; Barry, B. D.; Bi, X. H.; Dong, D. W. Chem. Commun. 2012, 48, 690.
[9] Knapp, J. M.; Zhu, J. S.; Wood, A. B.; Kurth, M. J. ACS Comb. Sci. 2012, 14, 85.
[10] Zhang, Z. G.; Fang, S. L.; Liu, Q. F.; Zhang, G. S. J. Org. Chem. 2012, 77, 7665.
[11] Liu, W. B.; Chen, C.; Zhang, Q.; Zhu, Z. B. Beilstein J. Org. Chem. 2011, 7, 1436.
[12] Liu, W. B.; Chen, C.; Zhang, Q.; Zhu, Z. B. Beilstein J. Org. Chem. 2012, 8, 344.
[13] Hu, W. J.; Deng, Z. H.; Chen, C.; Liu, W. B. J. Chem. Res. 2012, 36, 571.
[14] Zhang, Q.; Liu, W. B.; Chen, C.; Tan, L. Q. Chin. J. Chem. 2013, 31, 453.
[15] Fananás, F. J.; Arto, T.; Mendoza, A.; Rodrĺuez, F. Org. Lett. 2011, 13, 4184.
[16] Haga, Y.; Mizutani, S.; Naya, A.; Kishino, H.; Iwaasa, H.; Ito, M.; Ito, J.; Moriya, M.; Sato, N.; Takenaga, N.; Ishihara, A.; Tokita, S.; Kanatani, A.; Ohtake, N. Bioorg. Med. Chem. 2011, 19, 883.
[17] Hadden, M.; Deering, D. M.; Henderson, A. J.; Surman, M. D.; Luche, M.; Khmelnitsky, Y.; Vickers, S.; Viggers, J.; Cheetham, S.; Guzzo, P. R. Bioorg. Med. Chem. Lett. 2010, 20, 7020.
[18] Henderson, A. J.; Deering, D.; Grabowski, J. F.; Hadden, M.; Jiang, X.; Khmelnitsky, Y.; Luche, M.; Surman, M. D.; Cheetham, S.; Vickers, S.; Viggers, J.; Guzzo, P. R. Bioorg. Med. Chem. Lett. 2010, 20, 7024.
[19] Zhang, Z.; Fang, S.; Liu, Q.; Zhang, G. J. Org. Chem. 2012, 77, 7665.
[20] Pierce, J. B.; Ariyan, Z. S.; Ovenden, G. S. J. Med. Chem. 1982, 25, 131.
Outlines

/