Skip to main content
SpringerLink
Log in

Potassium Fluoride-Modified Clay as a Reusable Heterogeneous Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones

  • Published:
Russian Journal of Organic Chemistry Aims and scope Submit manuscript

Abstract

Potassium fluoride-modified clay collected from the region of Agadir (Morocco) was used as a hetaerogeneous catalyst in the one-pot synthesis of 3,4-dihydropyrimidine-2(1H)-one derivatives via the Biginelli reaction. The products were obtained with excellent yields (88–98%). The catalyst was characterized X-ray powder diffraction, Fourier-transform IR spectroscopy, scanning electron microscopy, differential thermal analysis, thermogravimetry, and Brunauer–Emmett–Teller (BET) analysis. Plausible reaction mechanisms for both reactions have been proposed. The catalyst can be recycled five times without loss of catalytic activity.

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

Similar content being viewed by others

References

  1. Saikia, M., Bhuyan, D., and Saikia, L., Appl. Catal., A, 2015, vol. 505, p. 501. doi 10.1016/j.apcata.2015.05.021

    Article  CAS  Google Scholar 

  2. Liberto, N.A., Silva, S.d.P., Fátima, Â.D., and Fernandes, S.A., Tetrahedron, 2013, vol. 69, p. 8245. doi 10.1016/j.tet.2013.07.024

    Article  CAS  Google Scholar 

  3. Biginelli, P., Gazz. Chem. Ital., 1893, vol. 23, p. 360.

    Google Scholar 

  4. Lin, H.X., Zhao, Q.J., Xu, B., and Wang, X.H., Chin. Chem. Lett., 2007, vol. 18, p. 502. doi 10.1016/j.cclet.2007.03.022

    Article  CAS  Google Scholar 

  5. Safari, J. and Gandomi-Ravandi, S., J. Mol. Struct., 2014, vols. 1065–1066, p. 241. doi 10.1016/j.molstruc.2014.02.035

    Article  Google Scholar 

  6. Rafiee, E. and Shahbazi, F., J. Mol. Catal. A: Chem., 2006, vol. 250, p. 57. doi 10.1016/j.molcata.2006.01.049

    Article  CAS  Google Scholar 

  7. Kouachi, K., Lafaye, G., Pronier, S., Bennini, L., and Menad, S., J. Mol. Catal. A: Chem., 2014, vol. 395, p. 210. doi 10.1016/j.molcata.2014.08.025

    Article  CAS  Google Scholar 

  8. Jetti, S.R., Bhatewara, A., Kadre, T., and Jain, S., Chin. Chem. Lett., 2014, vol. 25, p. 469. doi 10.1016/j.cclet.2013.12.022

    Article  CAS  Google Scholar 

  9. Konkala, K., Sabbavarapu, N.M., Katla, R., Durga, N.Y.V., Reddy, T.V.K., Devi, B.L.A.P., and Prasad, R.B.N., Tetrahedron Lett., 2012, vol. 53, p. 1968. doi 10.1016/j.tetlet.2012.02.018

    Article  CAS  Google Scholar 

  10. Brown, D., Comprehensive Heterocyclic Chemistry II, Katritzky, A.R., Rees, C.W., and Scriven, E.F.V., Eds., Oxford: Pergamon, 1996, vol. 3, p. 13.

    Google Scholar 

  11. Hassani, Z., Islami, M.R., and Kalantari, M., Bioorg. Med. Chem. Lett., 2006, vol. 16, p. 4479. doi 10.1016/j.bmcl.2006.06.038

    Article  CAS  Google Scholar 

  12. Gronnow, M.J., Luque, R., Macquarrie, D.J., and Clark, J.H., Green Chem., 2005, vol. 7, p. 552. doi 10.1039/b501130b

    Article  CAS  Google Scholar 

  13. Tu, S., Fang, F., Miao, C., Jiang, H., Feng, Y., Shi, D., and Wang, X., Tetrahedron Lett., 2003, vol. 44, p. 6153. doi 10.1016/S0040-4039(03)01466-7

    Article  CAS  Google Scholar 

  14. Bussolari, J.C. and McDonnel, P.A., J. Org. Chem., 2000, vol. 65, p. 6777. doi 10.1021/jo005512a

    Article  CAS  Google Scholar 

  15. Tayebee, R. and Ghadamgahi, M., Arab. J. Chem., 2017, vol. 10, p. S757. doi 10.1016/j.arabjc.2012.12.001

    Article  CAS  Google Scholar 

  16. Moosavifar, M., C. R. Chim., 2012, vol. 15, p. 444. doi 10.1016/j.crci.2011.11.015

    Article  CAS  Google Scholar 

  17. Tajbakhsh, M., Ranjbar, Y., Masuodi, A., and Khaksar, S., Chin. J. Catal., 2012, vol. 33, p. 1542. doi 10.1016/S1872-2067(11)60432-4

    Article  CAS  Google Scholar 

  18. Joseph, J.K., Jain, S.L., and Sain, B., J. Mol. Catal. A: Chem., 2006, vol. 247, p. 99. doi 10.1016/j.molcata.2005.11.028

    Article  CAS  Google Scholar 

  19. Mahdavinia, G.H. and Sepehrian, H., Chin. Chem. Lett., 2008, vol. 19, p. 1435. doi 10.1016/j.cclet.2008.09.028

    Article  CAS  Google Scholar 

  20. Nayak, P.S. and Singh, B.K., Bull. Mater. Sci., 2007, vol. 30, p. 235. doi 10.1007/s12034-007-0042-5

    Article  CAS  Google Scholar 

  21. Salman, M., Cizer, Ö., Pontikes, Y., Snellings, R., Vandewalle, L., Blanpain, B., and Balen, K.V., J. Hazard. Mater., 2015, vol. 286, p. 211. doi 10.1016/j.jhazmat.2014.12.046

    Article  CAS  Google Scholar 

  22. Bentahar, S., Lacherai, A., Dbik, A., El Messaoudi, N., and El Khomri, M., Iran. J. Energy Environ., 2015, vol. 6, p. 260. doi 10.5829/idosi.ijee.2015.06.04.03

    Google Scholar 

  23. Everett, D.H., Pure Appl. Chem., 1972, vol. 31, p. 577. doi 10.1351/pac197231040577

    Article  Google Scholar 

  24. Liu, H., Chen, W., Liu, C., Liu, Y., and Dong, C., Microporous Mesoporous Mater., 2014, vol. 194, p. 72. doi 10.1016/j.micromeso.2014.03.038

    Article  CAS  Google Scholar 

  25. Hafezi-Ardakani, M., Moztarzadeh, F., Rabiee, M., and Talebi, A.R., Ceram. Interfaces, 2011, vol. 37, p. 175. doi 10.1016/j.ceramint.2010.08.034

    Article  CAS  Google Scholar 

  26. Fazaeli, R., Tangestaninejad, S., Aliyan, H., and Moghadam, M., Appl. Catal., A, 2006, vol. 309, p. 44. doi 10.1016/j.apcata.2006.04.043

    Article  CAS  Google Scholar 

  27. Tamaddon, F. and Moradi, S., J. Mol. Catal. A: Chem., 2013, vol. 370, p. 117. doi 10.1016/j.molcata.2012.12.005

    Article  CAS  Google Scholar 

  28. Bentahar, S., Dbik, A., El Khomri, M., El Messaoudi, N., and Lacherai, A., Groundwater Sustainable Dev., 2018, vol. 6, p. 255. doi 10.1016/j.gsd.2018.02.002

    Article  Google Scholar 

  29. Wang, J-H., Zhang, E., Tang, G-M., Wang, Y-T., Cui, Y-Z., and Ng, S.W., J. Solid State Chem., 2016, vol. 241, p. 86. doi 10.1016/j.jssc.2016.05.009

    Article  CAS  Google Scholar 

  30. Angeletti, E., Canepa, C., Martinetti, G., and Venturello, P., J. Chem. Soc, Perkin Trans 1, 1989, p. 105. doi 10.1039/P19890000105

    Google Scholar 

  31. Ahmed, N. and Siddiqui, Z.N., J. Mol. Catal. A: Chem., 2014, vol. 387, p. 45. doi 10.1016/j.molcata.2014.02.019

    Article  CAS  Google Scholar 

  32. Ramiz, M.M.M., El-Sayed, W.A., Hagag, E., and Abdel-Rahman, A.A.-H., J. Heterocycl. Chem., 2011, vol. 48, p. 1028. doi 10.1002/jhet.686

    Article  CAS  Google Scholar 

  33. Ram, V.J., Arch. Pharm., 1990, vol. 323, p. 895. doi 10.1002/ardp.19903231103

    Article  CAS  Google Scholar 

Download references

Acknowledgments

The authors thank Prof. A. Khallaayoun and Prof. M. Ezahri for their valuable assistance.

Author information

Authors and Affiliations

  1. Laboratory of Applied Chemistry and Environment, Department of Chemistry, Faculty of Science, Ibn Zohr University, Agadir, Morocco

    S. Bentahar, A. Sabour, A. Dbik, M. El Khomri, N. El Messaoudi & A. Lacherai

  2. Team of Materials, Catalysis, and Valorization of Natural Resources, Department of Chemistry, Faculty of Science, Ibn Zohr University, Agadir, Morocco

    M. Ait Taleb & R. Mamouni

Authors
  1. S. Bentahar
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. M. Ait Taleb
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. A. Sabour
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. A. Dbik
    View author publications

    You can also search for this author in PubMed Google Scholar

  5. M. El Khomri
    View author publications

    You can also search for this author in PubMed Google Scholar

  6. N. El Messaoudi
    View author publications

    You can also search for this author in PubMed Google Scholar

  7. A. Lacherai
    View author publications

    You can also search for this author in PubMed Google Scholar

  8. R. Mamouni
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to S. Bentahar.

Ethics declarations

The authors declare no conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Bentahar, S., Taleb, M.A., Sabour, A. et al. Potassium Fluoride-Modified Clay as a Reusable Heterogeneous Catalyst for One-Pot Synthesis of 3,4-Dihydropyrimidin-2(1H)-ones. Russ J Org Chem 55, 1423–1431 (2019). https://doi.org/10.1134/S1070428019090240

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428019090240

Keywords

Search

Navigation