Iranian Journal of Chemistry

Iranian Journal of Chemistry

Design, synthesis and characterization of a magnetic covalent organic framework modified with sulfonic acid and investigation of its catalytic application in the preparation hexahydroquinoline and pyrazole containing derivatives

Document Type : Original Article

Authors
Meysam Yarie
Bahareh Vandaei
Morteza Torabi
Department of Organic Chemistry Faculty of Chemistry and Petroleum Sciences, Bu-Ali Sina University,
10.22036/cr.2024.441831.1232
Abstract
In the present research, first, the synthesis and characterization of a magnetic covalent organic framework modified with sulfonic acid were done. Then, the catalytic application of the prepared magnetic covalent organic framework modified with sulfonic acid was investigated in the preparation of some heterocyclic compounds containing hexahydroquinoline and pyrazole. The structure of the prepared the prepared magnetic covalent organic framework modified with sulfonic acid was confirmed by several methods such as Fourier-transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), derivative thermogravimetry (DTG), field-emission scanning electron microscopy (FE-SEM), energy-dispersive X-ray spectroscopy (EDS), elemental mapping, transmission electron microscopy (TEM), nitrogen absorption and desorption and vibrating-sample magnetometer (VSM). Then, the prepared structure was used in the preparation of hexahydroquinoline and pyrazole derivatives. Among the advantages of this research, are the multicomponent preparation of hexahydroquinoline and pyrazole derivatives in solvent-free conditions, high yield, and short reaction time, as well as recyclability and reusability of the catalyst.

Graphical Abstract

Design, synthesis and characterization of a magnetic covalent organic framework modified with sulfonic acid and investigation of its catalytic application in the preparation hexahydroquinoline and pyrazole containing derivatives
Keywords
Covalent organic framework
Hexahydroquinoline
Multicomponent reaction
Pyrazole

Subjects

  1. [1] A. P. Cote, A. I. Benin, N. W. Ockwig, M. OKeeffe, A. J. Matzger. O. M. Yaghi, Science, 310 (2005) 1166.

    [2] K. Geng, T. He, R. Liu, S. Dalapati, K. Tian Tan, Z. Li, S. Tao, Y. Gong, Q. Jiang, D. Jiang, Chem. Rev., 120

    (2020) 8814.

    [3] R. K. Sharma, P. Yadav, M. Yadav, R. Gupta, P. Rana, A. Srivastava, R. Zboril, R. S. Varma, M. Antonietti, M. B. Gawande, Mater. Horiz., 7(2020) 411.

    [4] K. Tian Tan, S. Ghosh, Z. Wang, F. Wen, D. Rodríguez-San-Miguel, J. Feng, N. Huang, W. Wang, F.

    Zamora, X. Feng, A. Thomas, D. Jiang, Nat. Rev. Methods Primers, 3 (2023) 1.

    [5] S. J. Lyle, P. J. Waller, O. M. Yaghi, Trends Chem., 1 (2019) 172. 

    [6] M. Yarie, Iran. J. Catal. Spotlight, 11 (2021) 89.

    [7] X. Liu, D. Huang, C. Lai, G. Zeng, L. Qin, H. Wang, H. Yi, B. Li, S. Liu, M. Zhang, R. Deng, Y. Fu, L. Li,

    1. Xue, S. Chen, Chem. Soc. Rev., 48 (2019) 5266.

    [8] X. Zhao, P. Pachfule, A. Thomas, Chem. Soc. Rev., 50 (2021) 6871.

    [9] B. S. Hote, T. A. Siddiqui and P. M. Pisal, Polycyclic Aromat. Compd., (2021) 1.

    [10] P. Choudhury, P. Ghosh B. Basu, Mol. Divers., 24 (2020) 283.

    [11] R. R. Raslan, S. A. Hessein, S. A. Fouad and N. A. Shmiess, J. Heterocycl. Chem., 59 (2021) 832.

    [12] H. Aghahosseini, M. R. Ranjbar, A. Ramazani, Chemistry Select, 5 (2020) 8415.

    [13] N. Hussain-Khil, A. Ghorbani-Choghamarani, M. Mohammadi, Sci. Rep., 11 (2021) 15657.

    [14] F. Fazl, M. Torabi, M. Yarie, M. A. Zolfigol, RSC Adv., 12 (2022) 16342.

    [15] M. Yarie, M. A. Zolfigol, Y. Bayat, A. Asgari, D. A. Alonso A. Khoshnood, RSC Adv., 6 (2016) 82842.

    [16] S. Kalhor, M. Yarie, M. Rezaeivala, M. A. Zolfigol, Res. Chem. Intermed., 45 (2019) 3453. 

    [17] M.E.A. Zaki, H.A. Soliman, O.A. Hiekal, A.E. Rashad, Z. Naturforsch., 61 (2006) 1.

    [18] N. Foloppe, L.M. Fisher, R. Howes, A. Potter, A.G. Robertson, A.E. Surgenor, Bioorg. Med. Chem., 14

    (2006) 4792.

    [19] N.R. Mohamed, N.Y. Khaireldin, A.F. Fahmy, A.A. El-Sayed, Der. Pharma. Chem., 2 (2010) 400.

    [20] S. Noura, M. Ghorbani, M. A. Zolfigol, M. Narimani, M. Yarie, M. Oftadeh, J. Mol. Liq., 271

    (2018) 778.

    [21] M. Yarie, M. A. Zolfigol, S. Baghery, D. A. Alonso, A. Khoshnood, Y. Bayat, A. Asgari, J. Mol.

    Liq., 271 (2018) 872.

    [22] N. S. Kaminwar, S. U. Tekale, A. B. Chidrawar, L. Kótai, R. P. Pawar, Lett. Appl. NanoBioSci., 9 (2020)

    1.  

    [23] I.A. Khodja, A. Fisli, O. Lebhour, R. Boulcina, B. Boumoud, A. Debache, Lett. Org. Chem. 13 85 (2016).

    [24] Y. Zhao, G. King, M. H. Kwan, A. J. Blacker, Org. Process Res. Dev., 20 (2016) 2012.

    [25] N. Bu, W.Y. Wu, P. Jiang, Z.Y. Zhan, J.L. Wan, Z. J. Wu, R. Wan, Chem. Pap., 75 (2021) 4493. 

    [26] A. Khazaei, M. Tavasoli, V. Jamshidi, F. G. Ghalil, A. R. Moosavi‐Zare, Appl. Organomet. Chem., 32

    (2018) e4368.

    [27] S. T., Fardood, A., Ramazani, S. Moradi, J. Sol-Gel Sci. Technol., 82 (2017) 432.

    [28] N. S. Kaminwar, S. U. Tekale, A. B. Chidrawar, L. Kótai, R. P. Pawar, Lett. Appl. NanoBioSci., 9 (2020)

    1.  

    [29] B. Eftekhari far, M. Nasr‐Esfahani, Appl. Organomet. Chem., 34 (2020) e5406.

    [30] S. Nazari, M. Keshavarz, Russ. J. Gen. Chem., 87 (2017) 539.

    [31] Z. Karimi-Jaberi, M. M. ReyazoShams, Heterocycl. Commun., 17 (2011) 5

Iranian Journal of Chemistry
Volume 6, Issue 2 - Serial Number 11
December 2023
Pages 169-179

  • Receive Date 15 February 2024
  • Revise Date 10 April 2024
  • Accept Date 17 April 2024