Skip to main content
SpringerLink
Log in

A comparative screening of the catalytic activity of nanocrystalline MIIZr4(PO4)6 ceramics in the one-pot synthesis of 1,6-diamino-4-aryl-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile derivatives

  • Published:
Research on Chemical Intermediates Aims and scope Submit manuscript

Abstract

A four-component reaction of hydrazine hydrate, ethyl cyanoacetate, malononitrile, and aromatic aldehydes was achieved in the presence of nanocrystalline MIIZr4(PO4)6 ceramics (MII: Mn, Fe, Co, Ni, Cu, Zn, Cd) as heterogeneous catalysts to produce N-amino-2-pyridones. The reactions were performed in the presence of different catalysts, and it is observed that CdZr4(PO4)6 nanocrystallines are the best catalysts among those examined. Atom economy, excellent yields in short times, high catalytic activity, recycling of catalyst, and environmental benignity are some of the important features of this protocol.

This is a preview of subscription content, log in via an institution to check access.

Access this article

Log in via an institution

Price excludes VAT (USA)
Tax calculation will be finalised during checkout.

Instant access to the full article PDF.

Institutional subscriptions

Scheme 1
Fig. 1
Scheme 2

Similar content being viewed by others

References

  1. J.P. Wan, Y. Liu, RSC Adv. 2, 9763 (2012)

    Article  CAS  Google Scholar 

  2. A. Kumar, M. Kumar Gupta, M. Kumar, D. Saxena, RSC Adv. 3, 1673 (2013)

    Article  CAS  Google Scholar 

  3. A. Banu, R.S. Lamani, I.A.M. Khazi, N. Shahina Begum, J. Saud. Chem. Soc. 18, 371 (2014)

    Article  CAS  Google Scholar 

  4. H. Shojaei, Z.L. Böhmer, P.V. Zezschwitz, J. Org. Chem. 72, 5091 (2007)

    Article  CAS  Google Scholar 

  5. P.S. Dragovich, T.J. Prins, R. Zhou, T.O. Johnson, Y. Hua, J. Med. Chem. 46, 4572 (2003)

    Article  Google Scholar 

  6. Q. Li, L.A. Mitscher, L.L. Shen, Med. Res. Rev. 20, 231 (2000)

    Article  CAS  Google Scholar 

  7. R.J. Cox, D. O’Hagan, J. Chem. Soc. Perkin Trans. 1, 2537 (1991)

    Article  Google Scholar 

  8. M. Nagarajan, X.S. Xiao, S. Antony, G. Kohlhagen, Y. Pommier, M. Cushman, J. Med. Chem. 46, 5712 (2003)

    Article  CAS  Google Scholar 

  9. R.K. Beckman, J.C. Potenza, E.J. Enholm, J. Org. Chem. 52, 469 (1987)

    Article  Google Scholar 

  10. Q.Y. Zhuang, J.N. Xu, S.J. Tu, R.H. Jia, J.Y. Zhang, C.M. Li, D.X. Zhou, Chin. J. Chem. 25, 1568 (2007)

    Article  CAS  Google Scholar 

  11. D.L. Comins, X. Chen, S.P. Joseph, Tetrahedron Lett. 37, 9275 (1996)

    Article  CAS  Google Scholar 

  12. M. Seifi, M. Khajehasani Rabori, H. Sheibani, Mod. Res. Catal. 2, 8 (2013)

    Article  CAS  Google Scholar 

  13. M.R.H. Elmoghayar, A.G.A. El-Agamey, M.Y. Abdel-Samad Nasr, M.M.M. Sallam, J. Heterocycl. Chem. 21, 1885 (1984)

    Article  CAS  Google Scholar 

  14. F.F. Abdel-Latif, R. Mekheimer, E.K. Ahmed, T.B. Abdel-Aleem, Pharmazie 48, 736 (1993)

    Google Scholar 

  15. A.H.M. Hussein, Heteroat. Chem. 8, 1 (1997)

    Article  CAS  Google Scholar 

  16. E.A. El-Rady, M.A. Khalil, J. Chin. Chem. Soc. 51, 779 (2004)

    Article  CAS  Google Scholar 

  17. W.M. Basyouni, Acta Chem. Slov. 50, 223 (2003)

    CAS  Google Scholar 

  18. E.M. Zayed, E.A. Hafez, S.A.S. Ghozlan, A.A.H. Ibrahim, Heterocycles 22, 2553 (1984)

    Article  CAS  Google Scholar 

  19. W.R. Abdel-Monem, Chem. Pap. 58, 276 (2004)

    CAS  Google Scholar 

  20. A.A. Harb, Chem. Pap. 58, 260 (2004)

    CAS  Google Scholar 

  21. M. Shankar Singh, S. Chowdhury, RSC Adv. 2, 4547 (2012)

    Article  Google Scholar 

  22. V. Estévez, M. Villacampa, J.C. Menéndez, Chem. Soc. Rev. 39, 4402 (2010)

    Article  Google Scholar 

  23. A. Bhunia, T. Kaicharla, D. Porwal, R.G. Gonnade, A.T. Biju, Chem. Commun. 50, 11389 (2014)

    Article  CAS  Google Scholar 

  24. F. Alonso, Y. Moglie, G. Radivoy, M. Yus, J. Org. Chem. 76, 8394 (2011)

    Article  CAS  Google Scholar 

  25. J. Safaei-Ghomi, H. Shahbazi-Alavi, S. Kalhor, Monatsh. Chem. (2016). doi:10.1007/s00706-016-1693-y

    Google Scholar 

  26. J. Safaei-Ghomi, P. Babaei, H. Shahbazi-Alavi, S. Zahedi, J. Saud. Chem. Soc. (2016). doi:10.1016/j.jscs.2016.01.003

    Google Scholar 

  27. M. Lakshmi Kantam, K.B. Shiva Kumar, C. Sridhar, Adv. Synth. Catal. 347, 1212 (2005)

    Article  Google Scholar 

  28. V. Polshettiwar, R.S. Varma, Green Chem. 12, 743 (2010)

    Article  CAS  Google Scholar 

  29. N. Gorodylova, V. Kosinova, Z. Dohnalova, P. Belina, P. Sulcova, Dyes Pigm. 98, 393 (2013)

    Article  CAS  Google Scholar 

  30. D.M. Liu, Mater. Chem. Phys. 36, 350 (1994)

    Article  CAS  Google Scholar 

  31. J. Safaei-Ghomi, M. Navvab, H. Shahbazi-Alavi, Ultrason. Sonochem. 31, 102 (2016)

    Article  CAS  Google Scholar 

  32. K. Tanabe, Solid Acids and Bases (Academic Press, New York, 1970)

    Book  Google Scholar 

  33. C. Zener, Phys. Rev. 82, 403 (1951)

    Article  CAS  Google Scholar 

  34. J.Y. Guo, C.X. Xu, Appl. Phys. A 102, 333 (2011)

    Article  CAS  Google Scholar 

  35. J. Ikhsan, B.B. Johnson, J.D. Wells, J. Colloid Interface Sci. 217, 403 (1999)

    Article  CAS  Google Scholar 

  36. S. Myradalyyev, T. Limpanuparb, X. Wang, H. Hirao, Polyhedron 52, 96 (2013)

    Article  CAS  Google Scholar 

  37. C.M. Aldao, I.M. Vitomirov, F. Xu, J.H. Weaver, Phys. Rev. B 37, 6019 (1988)

    Article  CAS  Google Scholar 

  38. A.A. Ensafi, E. Heydari-Bafrooei, B. Rezaei, Anal. Chem. 85, 991 (2013)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors acknowledge a reviewer who provided helpful insights. Meanwhile, the authors are grateful to the University of Kashan for supporting this work by Grant No: 159196/XXII. Also, the authors are grateful to Dr. Shayesteh Asadollahi for their help.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, 51167, Islamic Republic of Iran

    Javad Safaei-Ghomi & Hossein Shahbazi-Alavi

  2. Young Researchers and Elites Club, Kashan Branch, Islamic Azad University, Kashan, Islamic Republic of Iran

    Hossein Shahbazi-Alavi

  3. School of Chemistry, College of Science, University of Tehran, Tehran, 14155-6455, Islamic Republic of Iran

    Abolfazl Ziarati

Authors
  1. Javad Safaei-Ghomi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Hossein Shahbazi-Alavi
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Abolfazl Ziarati
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Javad Safaei-Ghomi.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 1527 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Safaei-Ghomi, J., Shahbazi-Alavi, H. & Ziarati, A. A comparative screening of the catalytic activity of nanocrystalline MIIZr4(PO4)6 ceramics in the one-pot synthesis of 1,6-diamino-4-aryl-2-oxo-1,2-dihydropyridine-3,5-dicarbonitrile derivatives. Res Chem Intermed 43, 91–101 (2017). https://doi.org/10.1007/s11164-016-2608-6

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-016-2608-6

Keywords

Search

Navigation