Cu-doped ZnO nanocrystalline powder as a catalyst for green and convenient multi-component synthesis of 1,4-dihydropyridine

Abstract

A simple, efficient, and convenient one-step method for synthesis of Hantzsch 1,4-dihydropyridine, using Cu-doped ZnO nanocrystalline powder as a catalyst is reported. The method offers several advantages including excellent yields, green solvent, easy work-up, simplicity in operation and catalyst reusability.

This is a preview of subscription content, access via your institution.

Scheme 1
Fig. 1
Fig. 2
Scheme 2

References

  1. 1.

    S. Jimenez-Abnso, H. Chavez, A. Estevez-Braan, A. Ravelo, G. Feresin, A. Tapia, Tetrahedron 64, 8938 (2008)

    Article  Google Scholar 

  2. 2.

    A. Chanda, V.V. Fokin, Chem. Rev. 109, 725 (2009)

    CAS  Article  Google Scholar 

  3. 3.

    Y. Sawada, H. Kayakiri, Y. Abe, T. Mizutani, N. Inamura, M. Asano, C. Hatori, I. Arsmori, T. Oku, H. Tanaka, J. Med. Chem. 47, 2853 (2004)

    CAS  Article  Google Scholar 

  4. 4.

    R.A. Janis, D.J. Triggle, J. Med. Chem. 26, 775 (1983)

    CAS  Article  Google Scholar 

  5. 5.

    R.H. Boecker, E.P. Guengerich, J. Med. Chem. 29, 1596 (1986)

    CAS  Article  Google Scholar 

  6. 6.

    M.F. Gordeev, D.V. Patel, E.M. Gordon, J. Org. Chem. 61, 924 (1996)

    CAS  Article  Google Scholar 

  7. 7.

    F.R. Buhler, W.J. Kiowski, J. Hypertens Suppl. 5, S3 (1987)

    Google Scholar 

  8. 8.

    S. Ko, C.F. Yao, Tetrahedron 62, 7293 (2006)

    CAS  Article  Google Scholar 

  9. 9.

    M.A. Chari, K. Syamasundar, Catal. Commun. 6, 624 (2005)

    Article  Google Scholar 

  10. 10.

    J.L. Donelson, R.A. Gibbs, S.K. De, J. Mol. Catal. A 256, 309 (2006)

    CAS  Article  Google Scholar 

  11. 11.

    N. Golego, S.A. Studenikin, M. Cocivera, J. Electrochem. Soc. 147, 1592 (2000)

    CAS  Article  Google Scholar 

  12. 12.

    Y. Lin, Z. Zhang, Z. Tang, F. Yuan, J. Li, Adv. Mater. Opt. Electron. 9, 205 (1999)

    CAS  Article  Google Scholar 

  13. 13.

    X. Wang, J. Song, J. Liu, Z.L. Wang, Science 316, 102 (2007)

    CAS  Article  Google Scholar 

  14. 14.

    K. Keren, R.S. Berman, E. Buchstab, U. Sivan, E. Braun, Science 302, 1380 (2003)

    CAS  Article  Google Scholar 

  15. 15.

    Z.L. Wang, Mater. Sci. Eng. 64, 33 (2009)

    Article  Google Scholar 

  16. 16.

    Y.M. Tao, S.Y. Ma, H.X. Chen, J.X. Meng, L.L. Hou, Y.F. Jia, X.R. Shang, Vacuum 85, 744 (2011)

    CAS  Article  Google Scholar 

  17. 17.

    Z. Zhang, J.B. Yi, J. Ding, L.M. Wong, H.L. Seng, S.J. Wang, J.G. Tao, G.P. Li, G.Z. Xing, T.C. Sum, C.H.A. Huan, T. Wu, J. Phys. Chem. C 112, 9579 (2008)

    CAS  Article  Google Scholar 

  18. 18.

    H. Alinezhad, S. Mohseni Tavakkoli, Sci World J 2013, 1 (2013)

    Article  Google Scholar 

  19. 19.

    J.J. Eynde, F. Delfosse, A. Mayence, Tetrahedron 51, 6511 (1995)

    Article  Google Scholar 

  20. 20.

    A. Debache, W. Ghalem, R. Boulcina, A. Belfaitah, S. Rhouati, B. Carboni, Tetrahedron Lett. 50, 5248 (2009)

    CAS  Article  Google Scholar 

  21. 21.

    B.M. Khadikar, V.G. Gaikar, A.A. Chitnavis, Tetrahedron Lett. 36, 8083 (1995)

    Article  Google Scholar 

  22. 22.

    A. Shaabani, A.H. Rezayan, A. Rahmati, Monatsh. Chem. 137, 77 (2006)

    CAS  Article  Google Scholar 

  23. 23.

    S.A. Kotharkar, D.B. Shinde, Ukr. Bioorg. Acta 1, 3 (2006)

    Google Scholar 

  24. 24.

    D. Bandyopadhyay, S. Maldonado, B.K. Banik, Molecules 17, 2643 (2012)

    CAS  Article  Google Scholar 

  25. 25.

    B. Datta, M. Afzal Pasha, Chin. J. Catal. 32, 1180 (2011)

    CAS  Article  Google Scholar 

  26. 26.

    P.P. Ghosh, P. Mukherjeea, A.R. Das, RSC Adv. 3, 8220 (2013)

    CAS  Article  Google Scholar 

  27. 27.

    G. Sabitha, K.R.G.S. Kiran, R.C. Srinivas, J.S. Yadav, Tetrahedron Lett. 44, 4129 (2003)

    CAS  Article  Google Scholar 

Download references

Acknowledgments

Financial support from the Research Council of University of Mazandran is gratefully acknowledged.

Author information

Affiliations

Authors

Corresponding author

Correspondence to Heshmatollah Alinezhad.

Rights and permissions

Reprints and Permissions

About this article

Verify currency and authenticity via CrossMark

Cite this article

Alinezhad, H., Mohseni Tavakkoli, S. Cu-doped ZnO nanocrystalline powder as a catalyst for green and convenient multi-component synthesis of 1,4-dihydropyridine. Res Chem Intermed 41, 5931–5940 (2015). https://doi.org/10.1007/s11164-014-1712-8

Download citation

Keywords

  • Cu-doped ZnO nanocrystalline powder
  • Multi-component
  • 1,4-Dihydropyridines
  • Hantzsch