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.
Similar content being viewed by others
REFERENCES
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
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
Nasr-Esfahani, M., Montazerozohori, M., and Abdizadeh, T., Chem. Pap., 2015, vol. 69, p. 1491. https://doi.org/10.1515/chempap-2015-0156
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
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
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
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
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
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
Bhragual, D.D., Kumar, N., and Drabu, S., J. Chem. Pharm. Res., 2010, vol. 2, p. 345.
Chawla, A., Sharma, A., and Kumar Sharma, A., Pharma Chem., 2012, vol. 4, p.116.
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
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
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
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
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
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
Sivakumar, K. Kathirvel, A., and Lalitha, A., Tetrahedron Lett., 2010, vol. 51, p. 3018. https://doi.org/10.1016/j.tetlet.2010.04.013
Davidson, D., Weiss, M., and Jelling, M., J. Org. Chem., 1937, vol. 2, p. 319. https://doi.org/10.1021/jo01227a004
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
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
Arabpourian, K. and Behbahani, F.K., Russ. J. Org. Chem., 2019, vol. 55, p. 682. https://doi.org/10.1134/S1070428019050166
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
Mirzaei, Z. and Behbahani, F.K., Heterocycl. Lett., 2018, vol. 8, p. 755.
Behbahani, F.K. and Ziaei, P., Chin. J. Chem., 2012, vol. 30, p. 65. https://doi.org/10.1002/cjoc.201180461
Behbahani, F.K. and Yektanezhad, T., Monatsh. Chem., 2012, vol. 143, p. 1529. https://doi.org/10.1007/s00706-012-0724-6
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
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
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
Derisavi, A. and Mohammadi, M.K., Int. J. Heterocycl. Chem., 2017, vol. 7, no. 2, p. 7.
Author information
Authors and Affiliations
Corresponding author
Ethics declarations
The authors declare the absence of conflict of interest.
Rights and permissions
About this article
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
Received:
Revised:
Accepted:
Published:
Issue Date:
DOI: https://doi.org/10.1134/S1070428020060160