Skip to main content
SpringerLink
Log in

A facile one-pot three component synthesis of 3, 4-dihydropyrimidin-2(1H)-ones or thiones promoted by a polymer-supported BF3 under solvent-free conditions

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

Abstract

In this study, cross-linked poly(4-vinylpyridine)-supported boron trifluoride, [P4-VP]-BF3, has been easily prepared and characterized by Fourier transform infrared (FT-IR), X-ray diffraction pattern, energy-dispersive X-ray spectroscopy analysis, scanning electron microscopy images and mapping. Afterward, catalytic activity of the obtained solid polymer-supported Lewis acid catalyst has been examined in Biginelli reaction for the synthesis of 3, 4-dihydropyrimidin-2(1H)-ones and 3, 4 dihydropyrimidin-2(1H)-thiones via one-pot three-component reaction between aryl aldehydes, β-dicarbonyl compounds and urea or thiourea under solvent-free conditions. The products were confirmed by their melting points (m.p.), FT-IR 1H and 13C nuclear magnetic resonance spectroscopy. The present procedure offers advantages, such as high to excellent yield (68–97% isolated yields), short reaction time (30–45 min), reusability of the catalyst, clean and fast work-up and easy separation of the catalyst by a simple filtration.

Graphical abstract

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
Fig. 2.
Fig. 3.
Scheme 2
Fig. 4
Fig. 5
Fig. 6
Fig. 7
Fig. 8
Fig. 9
Scheme 3

Similar content being viewed by others

References

  1. M. Ghorbani, S. Noura, M. Oftadeh, M.A. Zolfigol, M. HajiSoleimani, J. Mol. Liq. 212, 291 (2015)

    Article  CAS  Google Scholar 

  2. V. Polshettiwar, R.S. Varma, Pure Appl. Chem. 80, 777 (2008)

    Article  CAS  Google Scholar 

  3. S. Verma, S. Kumar, S.L. Jain, B. Sain, Org. Biomol. Chem. 9, 6943 (2011)

    Article  CAS  PubMed  Google Scholar 

  4. S. Verma, S.L. Jain, B. Sain, J. Org. Chem. 7, 1334 (2011)

    CAS  Google Scholar 

  5. H. Veisi, A. Maleki, S. Jahangard, Tetrahedron Lett. 56, 1882 (2015)

    Article  CAS  Google Scholar 

  6. S. Verma, S.L. Jain, Tetrahedron Lett. 53, 6055 (2012)

    Article  CAS  Google Scholar 

  7. S. Verma, S.L. Jain, Tetrahedron Lett. 53, 2595 (2012)

    Article  CAS  Google Scholar 

  8. A. Dömling, I. Ugi, Angew. Chem. 39, 3168 (2000)

    Article  Google Scholar 

  9. X.-M. Wang, H.-L. Ye, Z.-J. Qaun, X.-C. Wang, Res. Chem. Intermed. 39, 2357 (2013)

    Article  CAS  Google Scholar 

  10. P. Biginelli, Gazz. Chim. Ital. 23, 360 (1893)

    Google Scholar 

  11. E. Kolvari, M. Mirzaeeyan, J. Chem. 2013, 1 (2013)

    Article  CAS  Google Scholar 

  12. C.V. Reddy, M. Mahesh, P.V.K. Raju, T.R. Babu, V.V.N. Reddy, Tetrahedron Lett. 43, 2657 (2002)

    Article  CAS  Google Scholar 

  13. R.R. Nagawade, S.A. Kotharkar, D.B. Shinde, Mendeleev Commun. 15, 150 (2005)

    Article  CAS  Google Scholar 

  14. S.K. De, R.A. Gibbs, Synthesis 11, 1748 (2005)

    Article  CAS  Google Scholar 

  15. A. Shaabani, A. Bazgir, F. Teimouri, Tetrahedron Lett. 44, 857 (2003)

    Article  CAS  Google Scholar 

  16. M.G. Kulkarni, S.W. Chavhan, M.P. Shinde Beilstein, J. Org. Chem. 5, 4 (2009)

    Google Scholar 

  17. I. Cepanec, M. Litvic, M. Filipan-Litvic, I. Grungold, Tetrahedron 63, 11822 (2007)

    Article  CAS  Google Scholar 

  18. F. Xu, J.-J. Wang, Y.-P. Tian, Synth. Commun. 38, 1299 (2008)

    Article  CAS  Google Scholar 

  19. E.H. Hu, D.R. Sidler, U.H. Dolling, J. Org. Chem. 63, 3454 (1998)

    Article  CAS  Google Scholar 

  20. P. Salehi, M. Dabiri, M.A. Zolfigol, M.A. Bodaghi Fard, Tetrahedron Lett. 44, 2889 (2003)

    Article  CAS  Google Scholar 

  21. A.M. Elmaghraby, I.A. Mousa, A.A. Harb, M.Y. Mahgoub, ISRN Org. Chem. 2013, 1 (2013)

    Article  CAS  Google Scholar 

  22. F. Mohammadpour, M. Lashkari, J. Serb. Chem. Soc. 83, 673 (2018)

    Article  Google Scholar 

  23. E. Abbasi, F. Hatamjafari, Orient. J. Chem. 29, 731 (2013)

    Article  CAS  Google Scholar 

  24. B.F. Mirjalilia, A. Bamonirib, A. Akbari, J. Iran Chem. Soc. 8, S135 (2011)

    Article  Google Scholar 

  25. A. Zare, Z. Nasouri, J. Mol. Liq. 216, 364 (2016)

    Article  CAS  Google Scholar 

  26. J. Wu, X. Du, J. Ma, Y. Zhang, Q. Shi, L. Luo, B. Song, S. Yang, D. Hu, Green Chem. 16, 3210 (2014)

    Article  CAS  Google Scholar 

  27. B.J. Yao, W.X. Wu, L.G. Ding, Y.B. Dong, J. Org. Chem. 86, 3024 (2021)

    Article  CAS  PubMed  Google Scholar 

  28. U. Patel, B. Parmar, P. Patel, A. Dadhania, E. Suresh, Mater. Chem Front. 5, 304 (2021)

    Article  CAS  Google Scholar 

  29. D.P. Narayanan, A. Gopalakrishnan, Z. Yaakob, S. Sugunan, B.N. Narayanan, Arab. J. Chem 13, 318 (2017)

    Article  CAS  Google Scholar 

  30. A.N. Dadhania, V.K. Patel, D.K. Raval, J. Chem. Sci. 124, 926 (2012)

    Article  CAS  Google Scholar 

  31. A.N. Dadhania, V.K. Patel, D.K. Raval, J. Braz. Chem. Soc. 22, 511 (2011)

    Article  CAS  Google Scholar 

  32. C.C. Price, J.M. Ciskowski, J. Am. Chem. Soc. 60, 2499 (1938)

    Article  CAS  Google Scholar 

  33. J.A. Hyatt, P.W. Rayanolds, J. Org. Chem. 49, 384 (1984)

    Article  CAS  Google Scholar 

  34. J.S. Tou, W. Reusch, J. Org. Chem. 45, 5012 (1980)

    Article  CAS  Google Scholar 

  35. B. Sket, M.J. Zupan, Macromol. Sci. Chem. A19, 643 (1983)

    Article  CAS  Google Scholar 

  36. M.M. Lakouraj, M. Mokhtary, Monatsh Chem. 140, 53 (2009)

    Article  CAS  Google Scholar 

  37. M.A. Karimi Zarchi, Z. Hamidi, Res. Chem. Intermed. 44, 6995 (2018)

    Article  CAS  Google Scholar 

  38. M.K. Zarchi, S.S. Abadi, New J. Chem. 41, 10397 (2017)

    Article  Google Scholar 

  39. M.A. KarimiZarchi, R. Banihashemi, J. Sulfur Chem. 37, 282 (2016)

    Article  CAS  Google Scholar 

  40. M.A. KarimiZarchi, F. Nazem, J. Iran Chem. Soc. 11, 1731 (2014)

    Article  CAS  Google Scholar 

  41. M.A. KarimiZarchi, N. Ebrahimi, Phosphorus Sulfur 187, 1226 (2012)

    Article  CAS  Google Scholar 

  42. M.A. KarimiZarchi, Z. Mousavi, J. Polym. Res. 21, 330 (2014)

    Article  CAS  Google Scholar 

  43. M.A. Karimi Zarchi, A. Tabatabaei Bafghi, J. Sulfur Chem. 36, 403 (2015)

    Article  CAS  Google Scholar 

  44. M.A. Karimi Zarchi, R.Z. Escandari, J. Appl. Polym. Sci. 121, 1916 (2011)

    Article  CAS  Google Scholar 

  45. M.A. Karimi Zarchi, K. Behboodi, J. Polym. Res. 47, 4929 (2021)

    CAS  Google Scholar 

  46. Z. Hamidi, M.A. Karimi Zarchi, Res. Chem. Intermed. 44, 6995 (2018)

    Article  CAS  Google Scholar 

  47. S. Dehghani, M. Merajoddin, A. Zare, Asian J. Nanosci. Mater. 2, 367 (2019)

    CAS  Google Scholar 

  48. J. Mondal, T. Sen, A. Bhaumik, Dalton Trans. 41, 6173 (2012)

    Article  CAS  PubMed  Google Scholar 

  49. Y. Zhang, B. Wang, X. Zhang, J. Huang, C. Liu, Molecules 20, 3811 (2015)

    Article  CAS  PubMed  PubMed Central  Google Scholar 

  50. S. Besoluk, M. Kucukislamoglu, M. Zengin, M. Arslan, M. Nebioglu, Turk. J. Chem. 34, 411 (2010)

    CAS  Google Scholar 

  51. R.G. Fatemeh, F. Soghra, A. Hamid, Iran. J. Chem. Chem. Eng. 40, 3 (2021)

    Google Scholar 

  52. M. Moghaddas, A. Davoodnia, M.M. Heravi, N. Tavakoli-Hoseini, Chin. J. Catal. 33, 706 (2012)

    Article  CAS  Google Scholar 

  53. K.N. Handore, V.V. Chabukswar, D. Pawar, S. Dallavalle, Polym Plast Technol. Mater. 60, 306 (2020)

    Google Scholar 

  54. P.B. Das, I. Ruzmaikina, L.A. Belfiore, J. Polym. Sci. Polym. Phys. 38, 1931 (2000)

    Article  CAS  Google Scholar 

  55. A. Drelinkiewicz, M. Hasik, S. Quillard, C. Paluszkiewicz, J. Mol. Struct. 511, 205 (1999)

    Article  Google Scholar 

  56. M.A. Karimi Zarchi, A. Tarabsaz, J. Polym. Res. 20, 208 (2013)

    Article  CAS  Google Scholar 

  57. F. Hatamjafari, Org. Chem. Int. 2014, 1 (2014)

    Article  CAS  Google Scholar 

  58. M.M. Heravi, K. Bakhtiari, F.F. Bamoharram, Catal. Commun. 7, 373 (2006)

    Article  CAS  Google Scholar 

  59. M.A. Chari, K. Syamasundar, J. Mol. Catal. A Chem. 221, 137 (2004)

    Article  CAS  Google Scholar 

  60. H.R. Kalita, P. Phukan, Catal. Commun. 8, 179 (2007)

    Article  CAS  Google Scholar 

  61. W. Su, J. Li, Z. Zheng, Y. Shen, Tetrahedron Lett. 46, 6037 (2005)

    Article  CAS  Google Scholar 

  62. E. Kolvari, N. Koukabi, O. Armandpour, Tetrahedron 70, 1383 (2014)

    Article  CAS  Google Scholar 

  63. K.V.N.S. Srinivas, B. Das, Synthesis 2004(13), 2091 (2004)

    Article  CAS  Google Scholar 

  64. R. Varala, M.M. Alam, S.R. Adapa, Synlett 2002(1), 0067 (2002)

    Google Scholar 

  65. S.K. De, R.A. Gibbs, Synlett 2005(13), 1748 (2005)

    Google Scholar 

  66. J. Lu, H. Ma, Synlett 2000(1), 63 (2000)

    Article  Google Scholar 

  67. J.S. Yadav, B.V.S. Reddy, P. Sridhar, J.S.S. Reddy, K. Nagaiah, N. Lingaiah, P.S. Saiprasad, Eur. J. Org. Chem. 2004, 552 (2004)

    Article  CAS  Google Scholar 

  68. S. Chancharunee, P. Pinhom, M. Pohmakotr, P. Perlmutter, Synth. Commun. 39, 880 (2009)

    Article  CAS  Google Scholar 

Download references

Acknowledgements

The Research Council of Yazd University is gratefully acknowledged for the financial support of this work.

Author information

Authors and Affiliations

  1. Department of Organic Chemistry, Faculty of Chemistry, College of Science, Yazd University, P. O. Box 89195-741, Yazd, 8915813149, Iran

    Mohammad Ali Karimi Zarchi, Farhad Hajati & Bibi Fatemeh Mirjalili

Authors
  1. Mohammad Ali Karimi Zarchi
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Farhad Hajati
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Bibi Fatemeh Mirjalili
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Mohammad Ali Karimi Zarchi.

Ethics declarations

Conflict of interest

The authors state no conflict of interest.

Additional information

Publisher's Note

Springer Nature remains neutral with regard to jurisdictional claims in published maps and institutional affiliations.

Supplementary Information

Below is the link to the electronic supplementary material.

Supplementary file1 (DOCX 2881 KB)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Karimi Zarchi, M.A., Hajati, F. & Mirjalili, B.F. A facile one-pot three component synthesis of 3, 4-dihydropyrimidin-2(1H)-ones or thiones promoted by a polymer-supported BF3 under solvent-free conditions. Res Chem Intermed 48, 3449–3473 (2022). https://doi.org/10.1007/s11164-022-04764-z

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-022-04764-z

Keywords

Search

Navigation