Skip to main content
Log in

Synthesis of 8-Aryl-7H-acenaphtho[1,2-d]imidazoles Using Fe3O4 NPs@GO@C4H8SO3H as a Green and Recyclable Magnetic Nanocatalyst

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

Abstract

A general procedure has been developed for the rapid synthesis of 8-aryl-7H-acenaphtho[1,2-d]imidazoles in high yields using Fe3O4 NPs@GO@C4H8SO3H as a green and recyclable magnetic nanocatalyst under reflux conditions. The nanocatalyst was prepared and characterized by FT-IR, XRD, and EDX data. A variety of aromatic aldehydes underwent condensation with NH4OAc and acenaphthenequinone to give 8-aryl-7H-acenaphtho[1,2-d]imidazole derivatives. The use of magnetic nanoparticles, easy separation of the catalyst with an external magnet, high yields, and short reaction times are the main advantages of this catalytic method.

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

Access this article

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

Instant access to the full article PDF.

Scheme
Scheme
Fig. 1.
Fig. 2.
Fig. 3.
Scheme

Similar content being viewed by others

REFERENCES

  1. Zang, H., Su, Q., Mo, Y., Cheng, B. W., and Jun, S., Ultrason. Sonochem., 2010, vol. 17, p. 749. https://doi.org/10.1016/j.ultsonch.2010.01.015

    Article  PubMed  CAS  Google Scholar 

  2. Wan, Y., Liu, G., Zhao, L., Wang, H., Hung, S., Chen, L., and Wu, H., J. Heterocycl. Chem., 2014, vol. 51, p. 713. https://doi.org/10.1002/jhet.1751

    Article  CAS  Google Scholar 

  3. Nasr-Esfahani, M., Montazerozohori, M., and Abdizadeh, T., Chem. Pap., 2015, vol. 69, p. 1491. https://doi.org/10.1515/chempap-2015-0156

    Article  CAS  Google Scholar 

  4. Shingalapur, R.V., Hosamani, K.M., and Keri, R.S., Eur. J. Med. Chem., 2009, vol. 44, p. 4244. https://doi.org/10.1016/j.ejmech.2009.05.021

    Article  PubMed  CAS  Google Scholar 

  5. Ozkay, Y., Iskar, I., Incesu, Z., and Alkalin, G.E., Eur. J. Med. Chem., 2010, vol. 45, p. 3320. https://doi.org/10.1016/j.ejmech.2010.04.015

    Article  PubMed  CAS  Google Scholar 

  6. Tonelli, M., Simone, M., Tasso, B., Novelli, F., and Biodo, V., Bioorg. Med. Chem., 2010, vol. 18, p. 2937. https://doi.org/10.1016/j.bmc.2010.02.037

    Article  PubMed  CAS  Google Scholar 

  7. Mukherjee, A., Kumar, S., Seth, M., and Bhaduri, A.P., Indian J. Chem., Sect. B, 1989, vol. 28, p. 496. https://doi.org/10.1002/chin.198943134

    Article  Google Scholar 

  8. Hadizadeh, F., Hosseinzadeh, H., MotamedShariaty, V.S., Seifi, M., and Kazemi, S.H., Iran. J. Pharm. Res., 2008, vol. 7, p. 29. https://doi.org/10.22037/IJPR.2010.741

    Article  CAS  Google Scholar 

  9. Bhandari, K., Srinivas, N., and Marrapu, V.K., Bioorg. Med. Chem. Lett., 2010, vol. 20, p. 291. https://doi.org/10.1016/j.bmcl.2009.10.117

    Article  PubMed  CAS  Google Scholar 

  10. Bhragual, D.D., Kumar, N., and Drabu, S., J. Chem. Pharm. Res., 2010, vol. 2, p. 345.

    CAS  Google Scholar 

  11. Chawla, A., Sharma, A., and Kumar Sharma, A., Pharma Chem., 2012, vol. 4, p.116.

    CAS  Google Scholar 

  12. Padhy, A.K., Chetica, B., Mishara, S., Pati, A., and Iyer, P.K., Tetrahedron Lett., 2010, vol. 51, p. 2751. https://doi.org/10.1016/j.tetlet.2010.03.058

    Article  CAS  Google Scholar 

  13. Sadeghi, B., Mirjalili, B.B.F., and Hashemi, M.M., Tetrahedron Lett., 2008, vol. 49, p. 2575. https://doi.org/10.1016/j.tetlet.2008.02.100

    Article  CAS  Google Scholar 

  14. Karimi, A.R., Alimohammadi, Z., Azizian, J., Mohammadi, A.A., and Mohammadizadeh, M.R., Catal. Commun., 2006, vol. 7, p. 728. https://doi.org/10.1016/j.catcom.2006.04.004

    Article  CAS  Google Scholar 

  15. Heravi, H.H., Derikvand, F., and Bamoharram, F.F., J. Mol. Catal. A: Chem., 2007, vol. 263, p. 112. https://doi.org/10.1016/j.molcata.2006.08.048

    Article  CAS  Google Scholar 

  16. Samai, S., Nandi, G.C., Singh, P., and Singh, M.S., Tetrahedron, 2009, vol. 65, p. 10155. https://doi.org/10.1016/j.tet.2009.10.019

    Article  CAS  Google Scholar 

  17. Nagarapu, L., Apuri, S., and Kantevari, S., J. Mol. Catal. A: Chem., 2007, vol. 266, p. 104. https://doi.org/10.1016/j.molcata.2006.10.056

    Article  CAS  Google Scholar 

  18. Sivakumar, K. Kathirvel, A., and Lalitha, A., Tetrahedron Lett., 2010, vol. 51, p. 3018. https://doi.org/10.1016/j.tetlet.2010.04.013

    Article  CAS  Google Scholar 

  19. Davidson, D., Weiss, M., and Jelling, M., J. Org. Chem., 1937, vol. 2, p. 319. https://doi.org/10.1021/jo01227a004

    Article  CAS  Google Scholar 

  20. Wang, B., Gu, Y.L., Luo, C., Yang, T., Yang, L.M., and Suo, J.S., Tetrahedron Lett., 2004, vol. 45, p. 3417. https://doi.org/10.1016/j.tetlet.2004.03.012

    Article  CAS  Google Scholar 

  21. Chen, M.-N., Mo, L.-P., Cui, Z.-S., and Zhang, Z.-H., Curr. Opin. Green Sustainable Chem., 2019, vol. 15, p. 27. https://doi.org/10.1016/j.cogsc.2018.08.009

    Article  Google Scholar 

  22. Arabpourian, K. and Behbahani, F.K., Russ. J. Org. Chem., 2019, vol. 55, p. 682. https://doi.org/10.1134/S1070428019050166

    Article  CAS  Google Scholar 

  23. Heravi, M.M., Behbahani, F.K., Daraie, M., and Oskooie, H.A., Mol. Diversity, 2009, vol. 13, p. 375. https://doi.org/10.1007/s11030-009-9118-z

    Article  CAS  Google Scholar 

  24. Mirzaei, Z. and Behbahani, F.K., Heterocycl. Lett., 2018, vol. 8, p. 755.

    CAS  Google Scholar 

  25. Behbahani, F.K. and Ziaei, P., Chin. J. Chem., 2012, vol. 30, p. 65. https://doi.org/10.1002/cjoc.201180461

    Article  CAS  Google Scholar 

  26. Behbahani, F.K. and Yektanezhad, T., Monatsh. Chem., 2012, vol. 143, p. 1529. https://doi.org/10.1007/s00706-012-0724-6

    Article  CAS  Google Scholar 

  27. Fallah, N.S. and Mokhtary, M., J. Taibah Univ. Sci., 2015, vol. 9, p. 531. https://doi.org/10.1016/j.jtusci.2014.12.004

    Article  Google Scholar 

  28. Wang, Y., Sang, R., Zheng, Y., Guo, L., and Guan, M., Catal. Commun., 2017, vol. 89, p. 138. https://doi.org/10.1016/j.catcom.2016.09.027

    Article  CAS  Google Scholar 

  29. Nejadshafiee, V. and Islami, M.R., Mat. Sci. Eng. C., 2019, vol. 101, p. 42. https://doi.org/10.1016/j.msec.2019.03.081

    Article  CAS  Google Scholar 

  30. Derisavi, A. and Mohammadi, M.K., Int. J. Heterocycl. Chem., 2017, vol. 7, no. 2, p. 7.

    Google Scholar 

Download references

Author information

Authors and Affiliations

Authors

Corresponding author

Correspondence to F. K. Behbahani.

Ethics declarations

The authors declare the absence of conflict of interest.

Rights and permissions

Reprints and permissions

About this article

Check for updates. Verify currency and authenticity via CrossMark

Cite this article

Hasanzadeh, F., Behbahani, F.K. Synthesis of 8-Aryl-7H-acenaphtho[1,2-d]imidazoles Using Fe3O4 NPs@GO@C4H8SO3H as a Green and Recyclable Magnetic Nanocatalyst. Russ J Org Chem 56, 1070–1076 (2020). https://doi.org/10.1134/S1070428020060160

Download citation

  • Received:

  • Revised:

  • Accepted:

  • Published:

  • Issue Date:

  • DOI: https://doi.org/10.1134/S1070428020060160

Keywords:

Navigation