Skip to main content
SpringerLink
Log in

Eco-friendly highly efficient solvent free synthesis of benzimidazole derivatives over sulfonic acid functionalized graphene oxide in ambient condition

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

Abstract

Sulfonated graphene oxide (GO-HSO3) heterogeneous catalyst was prepared at molecular level and characterized by using various modern analytic and spectroscopic methods. Using prepared heterogeneous catalyst GO-HSO3, benzimidazole synthesis was carried out by means of reacting diamine and aldehyde at room temperature in solvent free condition. The catalyst GO-HSO3 showed tremendous catalytic activity in selective synthesis of benzimidazole, as a result 100 % conversion of reactants and up to 89.0 % yield of respective benzimidazole was achieved using 0.1 mg of catalyst in very short reaction duration. The GO-HSO3 catalyst was separated from the reaction mixture by simple filtration process at the end of reaction and reused for six successive cycles without noteworthy loss of catalytic activity and selectivity. Key advantageous of this protocol is high yield, low cost, and easy work-up procedure as well as short reaction time and solvent free condition. The present method is found eco-friendly, highly efficient, solvent free, high yielding, and clean method for the synthesis benzimidazole derivatives at room temperature.

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
Fig. 4
Fig. 5
Fig. 6
Scheme 2
Fig. 7

Similar content being viewed by others

References

  1. M. Hranjec, I. Piantanida, M. Kralj, L. Suman, K. Pavelic, G.K. Zamola, J. Med. Chem. 51, 4899 (2008)

    Article  CAS  Google Scholar 

  2. K. Yoshida, J. Chem. Soc. Chem. Commun., 1108 (1978)

  3. H.J. Seo, M. Song, S.H. Jin, J.H. Choi, S.J. Yun, Y.I. Kim, RSC Adv. 1, 755 (2011)

    Article  CAS  Google Scholar 

  4. D.D. Sun, W.Z. Wang, J.W. Mao, W.J. Mei, J. Liu, Bioorg. Med. Chem. Lett. 22, 102 (2012)

    Article  CAS  Google Scholar 

  5. L.B. Leroy, J.C. Drach, U.S. Patent US6455506 B1 (US 09/124,484), 2002

  6. P.K. Ranjith, P. Rajeesh, K.R. Haridas, N.Y. Susanta, T.N. Guru Row, R. Rishikesan, N. Suchetha Kumari, Bioorg. Med. Chem. Lett. 23, 5228 (2013)

    Article  CAS  Google Scholar 

  7. M.D. Poeta, W.A. Schell, C.C. Dykstra, S. Jones, R.R. Tidwell, A. Czarny, M. Bajic, M. Bajic, A. Kumar, D. Boykin, J.R. Perfect, Antimicrob. Agents Chemother. 42, 2495 (1998)

    Google Scholar 

  8. Y. Tong, J.J. Bouska, P.A. Ellis, E.F. Johnson, J. Leverson, X. Liu, P.A. Marcotte, A.M. Olson, D.J. Osterling, M. Przytulinska, L.E. Rodriguez, Y. Shi, N. Soni, J. Stavropoulos, S. Thomas, C.K. Donawho, D.J. Frost, Y. Luo, V.L. Giranda, T.D. Penning, J. Med. Chem. 52, 6803 (2009)

    Article  CAS  Google Scholar 

  9. R. Lemura, T. Kawashima, T. Fukuda, K. Ito, G. Tsukamoto, J. Heterocycl. Chem. 24, 31 (2009)

    Google Scholar 

  10. M.C. Sharma, D.V. Kohli, Arabian J. Chem. (2011). doi:10.1016/j.arabjc.2011.04.016

    Google Scholar 

  11. S.M. Sondhi, N. Singh, A. Kumar, O. Lozach, L. Meijer, Bioorg. Med. Chem. 14, 3758 (2006)

    Article  CAS  Google Scholar 

  12. T. Iwahi, H. Satoh, M. Nakao, T. Iwasaki, T. Yamazaki, K. Kubo, T. Tamura, A. Imada, Antimicrob. Agents Chemother. 35, 490 (1991)

    Article  CAS  Google Scholar 

  13. H.A. Barker, R.D. Smyth, H. Weissbach, J.I. Toohey, J.N. Ladd, B.E. Volcani, J. Biol. Chem. 235, 480 (1960)

    CAS  Google Scholar 

  14. M.A. Phillips, J. Chem. Soc., 172 (1928)

  15. M. Kidwai, A. Jahan, D. Bhatnagar, J. Chem. Sci. 122, 607 (2012)

    Article  Google Scholar 

  16. P. Sun, Z. Hu, J. Heterocycl. Chem. 43, 773 (2006)

    Article  CAS  Google Scholar 

  17. B. Sadeghi, M.G. Nejad, J. Chem. 2013 (2013) (Article ID: 581465)

  18. R. Trivedi, S.K. De, R.A. Gibbs, J. Mol. Catal. A: Chem. 245, 8 (2006)

    Article  CAS  Google Scholar 

  19. R.G. Jacob, L.G. Dutra, C.S. Radatz, S.R. Mendes, G. Perin, E. Lenardao, Tetrahedron Lett. 50, 1495 (2009)

    Article  CAS  Google Scholar 

  20. R.K. Kumar, P.V.V. Satyanarayana, S.B. Reddy, Arch. Appl. Sci. Res. 4, 1517 (2012)

    Google Scholar 

  21. C. Mukhopadhyay, P.K. Tapaswi, Tetrahedron Lett. 49, 6237 (2008)

    Article  CAS  Google Scholar 

  22. K. Bahrami, M.M. Khodaei, F. Naali, Synlett 04, 569 (2009)

    Article  Google Scholar 

  23. S. Lin, L.H. Yang, Tetrahedron Lett. 46, 4215 (2005)

    Google Scholar 

  24. K.B. Dhopte, R.S. Zambare, A.V. Patwardhana, P.R. Nemade, RSC Adv. 6, 8164 (2016)

    Article  CAS  Google Scholar 

  25. R.S. Harapanhalli, L.W. McLaughlin, R.W. Howell, D.V. Rao, S.J. Adelstein, A.I. Kassis, J. Med. Chem. 39, 4804 (1996)

    Article  CAS  Google Scholar 

  26. J.J. Vanden Eynde, F. Delfosse, P. Lor, Y.V. Haverbeke, Tetrahedron 51, 5813 (1995)

    Article  CAS  Google Scholar 

  27. A.H. Jadhav, H. Kim, RSC Adv. 3(15), 5131 (2013)

    Article  CAS  Google Scholar 

  28. A.H. Jadhav, A. Chinnappan, R.H. Patil, W.J. Chung, H. Kim, Chem. Eng. J. 236, 300 (2014)

    Article  CAS  Google Scholar 

  29. A.H. Jadhav, A. Chinnappan, V. Hiremath, J.G. Seo, J. Nanosci. Nanotechnol. 15(10), 8243 (2015)

    Article  CAS  Google Scholar 

  30. A.H. Jadhav, A.C. Lim, G.M. Thorat, H.S. Jadhav, J.G. Seo, RSC Adv. 6, 31675 (2016)

    Article  CAS  Google Scholar 

  31. D.R. Dreyer, S. Park, C.W. Bielawski, R.S. Ruoff, Chem. Soc. Rev. 39, 228 (2010)

    Article  CAS  Google Scholar 

  32. M.J. Allen, V.C. Tung, R.B. Kaner, Chem. Rev. 110, 132 (2010)

    Article  CAS  Google Scholar 

  33. M. Mirza-Aghayan, R. Boukherroub, M. Rahimifard, Turk. J. Chem. 38, 859 (2014)

    Article  CAS  Google Scholar 

  34. M. Mirza-Aghayan, M. Alizadeh, M.M. Tavana, R. Boukherroub, Tetrahedron Lett. 55, 6694 (2014)

    Article  CAS  Google Scholar 

  35. M.M. Aghayan, M.M. Tavana, R. Boukherroub, Ultrason. Sonochem. 29, 371 (2016)

    Article  Google Scholar 

  36. J. Ji, G. Zhang, H. Chen, S. Wang, G. Zhang, F. Zhang, X. Fan, Chem. Sci. 2, 484 (2011)

    Article  CAS  Google Scholar 

  37. A.H. Jadhav, K. Lee, S. Koo, J.G. Seo, RSC Adv. 5(33), 26197 (2015)

    Article  CAS  Google Scholar 

  38. A.H. Jadhav, G.M. Thorat, K. Lee, A.C. Lim, H. Kang, J.G. Seo, Catal. Today 265, 56 (2016)

    Article  CAS  Google Scholar 

  39. A.H. Jadhav, A. Chinnappan, R.H. Patil, S.V. Kostjuk, H. Kim, Chem. Eng. J. 240, 228 (2014)

    Article  CAS  Google Scholar 

Download references

Acknowledgments

Authors would like to thanks Council of Scientific and Industrial Research (CSIR), New Delhi, India for the Junior Research Fellowship (JRF) and Senior Research Fellowship (SRF) program for financial support. Authors also would like to thanks for the research facility provided by Dr. Jeong Gil Seo, via through the National Research Foundation of Korea (NRF) funded by the Ministry of Education (No. 2009-0093816) and Myongji Research Fund-2014.

Author information

Author notes

    Authors and Affiliations

    1. Department of Chemistry, Maharashtra Udayagiri Mahavidyalaya, Udgir, Latur, 413517, India

      Mantosh B. Swami, Hanmant G. Ghuge & Sudhakar G. Patil

    2. Department of Chemistry, Mahatma Basweshwar Mahavidyalay, Latur, Latur, 413512, India

      Mantosh B. Swami

    3. Department of Energy Science and Technology, Energy and Environment Fusion Technology Center, Myongji University, Myongji-ro 116, Cheoin-gu, Yongin-si, Gyeonggi-do, 449-728, Republic of Korea

      Arvind H. Jadhav

    4. Department of Chemistry, Shri Madhavrao Patil Mahavidyalaya, Murum, Osmanabad, 413605, India

      Sushil R. Mathpati

    Authors
    1. Mantosh B. Swami
      View author publications

      You can also search for this author in PubMed Google Scholar

    2. Arvind H. Jadhav
      View author publications

      You can also search for this author in PubMed Google Scholar

    3. Sushil R. Mathpati
      View author publications

      You can also search for this author in PubMed Google Scholar

    4. Hanmant G. Ghuge
      View author publications

      You can also search for this author in PubMed Google Scholar

    5. Sudhakar G. Patil
      View author publications

      You can also search for this author in PubMed Google Scholar

    Corresponding authors

    Correspondence to Arvind H. Jadhav or Sudhakar G. Patil.

    Additional information

    Mantosh B. Swami and Arvind H. Jadhav have contributed equally to this work.

    Rights and permissions

    Reprints and permissions

    About this article

    Check for updates. Verify currency and authenticity via CrossMark

    Cite this article

    Swami, M.B., Jadhav, A.H., Mathpati, S.R. et al. Eco-friendly highly efficient solvent free synthesis of benzimidazole derivatives over sulfonic acid functionalized graphene oxide in ambient condition. Res Chem Intermed 43, 2033–2053 (2017). https://doi.org/10.1007/s11164-016-2745-y

    Download citation

    • Received:

    • Accepted:

    • Published:

    • Issue Date:

    • DOI: https://doi.org/10.1007/s11164-016-2745-y

    Keywords

    Search

    Navigation