Skip to main content
SpringerLink
Log in

Propyl–SO3H functionalized SBA-15: Microwave-mediated green synthesis of biologically active multi-substituted imidazole scaffolds

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

Abstract

Propylsulfonic acid functionalized Santa Barbara Amorphous-15 (SBA-15–Pr–SO3H) catalyst has been synthesized using a surface modification of mesoporous SBA-15 via the one-pot co-condensation method. The synthesized SBA-15–Pr–SO3H has been characterized by peculiar characterization techniques such as small- and wide-angle XRD, SEM–EDX, TEM, TG–DTA, acidity, FT-IR, Py-FT-IR and BET surface area analysis. The catalytic activity of synthesized catalyst has been studied towards solvent-free MW irradiation for the green and rapid synthesis of multi-substituted imidazoles, [2,4,5-triphenyl-1(H)-imidazole (tri-imidazole) and 1-benzyl-2,4,5-triphenyl-1H-imidazole (tetra-imidazole)]. The SBA-15–Pr–SO3H catalyst was found to be an efficient and recyclable solid acid catalyst and this solvent-free MW protocol afforded products in good to excellent yields of both, tri and tetra imidazoles (> 95%) within shorter reaction time (3 min) at 600 W as compared to the SBA-15 and other existing protocols. The applicability of this protocol was further explored by conducting the experiments in the presence of varied solvents and substituted aldehydes to generate a library of both, tri- and tetra-imidazole scaffolds. The catalyst was found to be reusable up to several runs without loss of its catalytic activity. This report allows the rapid and scalable access to a variety of multi-substituted imidazoles using SBA-15–Pr–SO3H, as heterogeneous catalyst.

Graphical abstract

SBA-15–Pr–SO3H catalyzed solvent-free MW assisted green synthesis of multi-substituted imidazoles via MCRs.

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
Scheme 2
Fig. 1
Fig. 2
Fig. 3
Fig. 4
Fig. 5
Fig. 6
Fig. 7

Similar content being viewed by others

References

  1. J.P. Tierney, P. Lidstrom, B. Wathey, J. Westman, Tetrahedron 57, 9225 (2005)

    Google Scholar 

  2. D.M. D’Souza, T.J.J. Müller, Chem. Soc. Rev. 36, 1095 (2007)

    Article  PubMed  Google Scholar 

  3. A. Rivera-Hernández, I.S. López-Jimeno, G.A. Carmona-Reyes, R. Alfredo-Toscano, J.G. Penieres-Carrillo, C. Álvarez-Toledano, Tetrahedron Lett. 56, 4829 (2015)

    Article  CAS  Google Scholar 

  4. J.J. Gabla, S.R. Mistry, K.C. Maheria, Catal. Sci. Technol. 7, 5154 (2017)

    Article  CAS  Google Scholar 

  5. A.R. Karimi, Z. Alimohammadi, M.M. Amini, Mol. Divers. 14, 635 (2010)

    Article  CAS  PubMed  Google Scholar 

  6. B. Radziszewski, Chem. Ber. 15, 1493 (1882)

    Article  Google Scholar 

  7. F. Japp, H. Robenson, Chem. Ber. 15, 1268 (1882)

    Article  Google Scholar 

  8. G. Drefahl, H. Herma, Chem. Ber. 93, 486 (1960)

    Article  CAS  Google Scholar 

  9. I. Lantos, W.Y. Zhang, X. Shui, D.S. Eggleston, J. Org. Chem. 58, 7092 (1993)

    Article  CAS  Google Scholar 

  10. C. Zhang, E.J. Moran, T.F. Woiwode, K.M. Short, A.M.M. Mjalli, Tetrahedron Lett. 37, 751 (1996)

    Article  CAS  Google Scholar 

  11. H. B. Lee, S. Balasubramanian, Org. Lett. 2, 323 (2000)

    Article  CAS  PubMed  Google Scholar 

  12. C.F. Claiborne, N.J. Liverton, K.T. Nguyen, Tetrahedron Lett. 39, 8939 (1998)

    Article  CAS  Google Scholar 

  13. J.J. Gabla, S.R. Mistry, K.C. Maheria, J. Catal. Catal. 4, 20 (2017)

    CAS  Google Scholar 

  14. S. Balalaie, A. Arabanian, Green Chem. 2, 274 (2000)

    Article  CAS  Google Scholar 

  15. M.C. Road, S. Nagar, M.L. Limited, A. Industrial, B. Village, J. Mandal, Rasayan J. Chem. 3, 335 (2010)

    Google Scholar 

  16. H.R. Shaterian, M. Ranjbar, J. Mol. Liq. 160, 40 (2011)

    Article  CAS  Google Scholar 

  17. S.A. Siddiqui, U.C. Narkhede, S.S. Palimkar, T. Daniel, R.J. Lahoti, K.V. Srinivasan, Tetrahedron 61, 3539 (2005)

    Article  CAS  Google Scholar 

  18. J. Safari, S. Gandomi-ravandi, Z. Akbari, J. Adv. Res. 4, 509 (2013)

    Article  PubMed  Google Scholar 

  19. J. Wang, R. Mason, D. VanDerveer, K. Feng, X.R. Bu, J. Org. Chem. 68, 5415 (2003)

    Article  CAS  PubMed  Google Scholar 

  20. A. Shaabani, A. Rahmati, J. Mol. Catal. A Chem. 249, 246 (2006)

    Article  CAS  Google Scholar 

  21. D. Morawala, A. Dalai, K.C. Maheria,J. Por. Mater. 26, (2018)

  22. S.R. Mistry, K.C. Maheria, J. Catal. Catal. 1, 1 (2014)

    Google Scholar 

  23. S.R. Mistry, K.C. Maheria, J. Mol. Catal. A Chem. 355, 210 (2012)

    Article  CAS  Google Scholar 

  24. S.R. Mistry, R.S. Joshi, K.C. Maheria, J. Chem. Sci. 123, 427 (2011)

    Article  CAS  Google Scholar 

  25. S.R. Mistry, R.S. Joshi, S.K. Sahoo, K.C. Maheria, Catal. Lett. 141, 1541 (2011)

    Article  CAS  Google Scholar 

  26. H. Chaudhuri, S. Dash, A. Sarkar, Ind. Eng. Chem. Res. 56, 2943 (2017)

    Article  CAS  Google Scholar 

  27. L. Cao, Z. Jia, S. Ji, J. Hu, J. Nat. Gas Chem. 20, 377 (2011)

    Article  CAS  Google Scholar 

  28. V.F. Vavsari, G. Mohammadi Ziarani, A. Badiei, RSC Adv. 5, 91686 (2015)

    Article  CAS  Google Scholar 

  29. R.H. Vekariya, H.D. Patel, Synth. Commun. 45, 1031 (2015)

    Article  CAS  Google Scholar 

  30. K.A. Shah, J.K. Parikh, K.C. Maheria, Catal. Today 237, 29 (2014)

    Article  CAS  Google Scholar 

  31. A. Teimouri, A.N. Chermahini, J. Mol. Catal. A Chem. 346, 39 (2011)

    Article  CAS  Google Scholar 

  32. S. Samai, G.C. Nandi, P. Singh, M.S. Singh, Tetrahedron 65, 10155 (2009)

    Article  CAS  Google Scholar 

  33. B. Maleki, H. Keshvari Shirvan, F. Taimazi, E. Akbarzadeh, Int. J. Org. Chem. 2, 93 (2012)

    Article  CAS  Google Scholar 

  34. K. Babu, V. Surendhar, Hetero. Lett. 4, 235 (2014)

    Google Scholar 

  35. B.F. Mirjalili, A.H. Bamoniri, L. Zamani, Sci. Iran. 19, 565 (2012)

    Article  CAS  Google Scholar 

  36. R. Yan, L. Ming, Z. Zong-Ze, Molecules 20, 20286 (2015)

    Article  CAS  Google Scholar 

  37. N.M. Kalkhorani, M.M. Heravi,J. Chem. 1 (2013)

  38. H.T. Najmeh Zahedi, A. Javid, M. Kazem Mohammadi, Bull. Chem. Soc. Ethiop. 32, 157 (2018)

    Article  CAS  Google Scholar 

  39. K.F. Shelke, S.B. Sapkal, G.K. Kakade, B.B. Shingate, M.S. Shingare, Green Chem. Lett. Rev. 3, 27 (2010)

    Article  CAS  Google Scholar 

  40. G.K. Sharma, N.K. Sharma, D. Pathak, Ind. J. Chem. 52B, 266 (2013)

    CAS  Google Scholar 

Download references

Acknowledgements

The authors are grateful to the director, SVNIT, Surat, for providing research and financial assistance. This research was supported by a research grant for assistant professor No: Dean (R&C)/1503/2013-14 from Sardar Vallabhbhai National Institute of Technology, Surat (SVNIT, Surat). The authors would also like to thank IISER-Mohali, India, for SAXS characterization facility.

Author information

Authors and Affiliations

  1. Applied Chemistry Department, Sardar Vallabhbhai National Institute of Technology (SVNIT), Surat, Gujarat, 395007, India

    Jenifer J. Gabla, Dharmesh R. Lathiya, Akash A. Revawala & Kalpana C. Maheria

Authors
  1. Jenifer J. Gabla
    View author publications

    You can also search for this author in PubMed Google Scholar

  2. Dharmesh R. Lathiya
    View author publications

    You can also search for this author in PubMed Google Scholar

  3. Akash A. Revawala
    View author publications

    You can also search for this author in PubMed Google Scholar

  4. Kalpana C. Maheria
    View author publications

    You can also search for this author in PubMed Google Scholar

Corresponding author

Correspondence to Kalpana C. Maheria.

Electronic supplementary material

Below is the link to the electronic supplementary material.

Supplementary material 1 (DOCX 98 kb)

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Gabla, J.J., Lathiya, D.R., Revawala, A.A. et al. Propyl–SO3H functionalized SBA-15: Microwave-mediated green synthesis of biologically active multi-substituted imidazole scaffolds. Res Chem Intermed 45, 1863–1881 (2019). https://doi.org/10.1007/s11164-018-3707-3

Download citation

  • Received:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1007/s11164-018-3707-3

Keywords

Search

Navigation