Preparation, Characterization and Application of a Novel Organic-Inorganic Hybrid Magnetic Nanomaterial as a Highly Efficient Catalyst for the Synthesis of Bis-Coumarins

الموضوعات : Iranian Journal of Catalysis

Marziyeh Barzegar ¹ (Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran.)
Abdolkarim Zare ² (Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran.)
Aysoda Ghobadpoor ³ (Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran.)
Manije Dianat ⁴ (Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran.)

تاريخ الإرسال : 12 الأربعاء , رجب, 1442 تاريخ التأكيد : 01 الثلاثاء , جمادى الثانية, 1443 تاريخ الإصدار : 28 الثلاثاء , رجب, 1443

الکلمات المفتاحية: Solvent-free, Organic-inorganic hybrid magnetic nanomaterial, Nano-[Fe3O4@SiO2@R-NMe2][FeCl4] (nano-[FSRN][FeCl4]), Dual-functional catalyst, Bis-coumarin,

ملخص المقالة :

A novel organic-inorganic hybrid magnetic nanomaterial, namely nano-[Fe3O4@SiO2@R-NMe2][FeCl4] (nano-[FSRN][FeCl4]) was prepared, and characterized by EDX, elemental mapping, FE-SEM, FT-IR, XRD, VSM, TG and DTG analyses. Then, it was applied as a highly efficient and magnetically recyclable catalyst for the solvent-free synthesis of bis-coumarins from 4-hydroxycoumarin (2 eq.) and arylaldehydes (1 eq.). NMe2 is a basic group, and FeCl4− is a Lewis acid; thus, nano-[FSRN][FeCl4] can act as a dual-functional catalyst; based on this and the literature, a plausible mechanism was proposed for the reaction.

المصادر:

[1] S. Montes, H. Maleki, Colloidal Metal Oxide Nanoparticles: Synthesis, Characterization and Applications, S. Thomas, A. T. Sunny, P. Velayudhan (Ed.), Elsevier (2020), https://doi.org/10.1016/C2016-0-03725-7.

[2] C. Sanchez, B. Julián, P. Belleville, M. Popall, J. Mater. Chem. 15 (2005) 3559-3592.

[3] C.-H. Yang, Y.-W. Pan, J.-J. Guo, T.-H. Young, W.-Y. Chiu, K.-H. Hsieh, J. Polym. Res. 23 (2016) 29.

[4] P. Huang, Y. Chen, H. Lin, L. Yu, L. Zhang, L. Wang, Y. Zhu, J. Shi, Biomaterials 125 (2017) 23-37.

[5] B. Zhang, Y. Zhang, Z. Wang, D. Yang, Z. Gao, D. Wang, Y. Guo, D. Zhu, T. Mori, Dalton Trans. 45 (2016) 16561-16565.

[6] X. Liu, C. Ji, Z. Wu, L. Li, S. Han, Y. Wang, Z. Sun, J. Luo, Chem. Eur. J. 25 (2019) 2610-2615.

[7] F. Jalili, M. Zarei, M. A. Zolfigol, S. Rostamnia, A. R. Moosavi-Zare, Micropor. Mesopor. Mater. 294 (2020) 109865.

[8] A. Zare, F. Monfared, S. S. Sajadikhah, Appl. Organomet. Chem. 34 (2020) e6046.

[9] P. Moradi, M. Hajjami, New J. Chem. 45 (2021) 2981-2994.

[10] A. Zare, R. Khanivar, N. Irannejad-Gheshlaghchaei, M. H. Beyzavi, ChemistrySelect 4 (2019) 3953-3960.

[11] M. Shekouhy, R. Kordnezhadian, A. Khalafi-Nezhad, J. Iran. Chem. Soc. 15 (2018) 2357-2368.

[12] A. Shamaei, B. Mahmoudi, M. Kazemnejadi, M. A. Nasseri, Appl. Organomet. Chem. 34 (2020) e5997.

[13] A. Zare, M. Dianat, M. M. Eskandari, New J. Chem. 44 (2020) 4736-4743.

[14] J. Choi, J. S. Han, K. Hong, S. Y. Kim, H. W. Jang, Adv. Mater. 30 (2018) 1704002.

[15] T. Feng, B. Lin, S. Zhang, N. Yuan, F. Chu, M. A. Hickner, C. Wang, L. Zhu, J. Ding, J. Membr. Sci. 508 (2016) 7-14.

[16] G. Mohammadi Ziarani, V. Fathi Vavsari, A. Badiei, J. Afshani, P. Gholamzadeh, S. Balalaie, F. Faridbod, M. R. Ganjali, J. Iran. Chem. Soc. 15 (2018) 211-221.

[17] V. Mohammadi, M. Tabatabaee, A. Fadaei, S. A. Mirhoseini, Iran. J. Catal. 10 (2020 209-218.

[18] Z. Karimi Ghezeli, M. Hekmati, H. Veisi, Appl. Organomet. Chem. 33 (2019) e4833.

[19] R. Doaga, T. McCormac, E. Dempsey, Microchim. Acta 187 (2020) 225.

[20] F. Gao, ChemistrySelect 4 (2019) 6805-6811.

[21] S. Azizi, H. Nosrati, H. Danafar, Appl. Organomet. Chem. 34 (2020) e5479.

[22] R. K. Gautam, I. Tiwari, Chemosphere 245 (2020) 125553.

[23] J. Safari, M. Tavakoli, M. A. Ghasemzadeh, Polyhedron 182 (2020) 114459.

[24] M. A. Ghasemzadeh, B. Mirhosseini-Eshkevari, M. Tavakoli, F. Zamani, Green Chem. 22 (2020) 7265-7300.

[25] S. Sajjadifar, I. Amini, M. Karimian, Iran. J. Catal. 11 (2021) in press.

[26] F. Gholami Orimi, B. Mirza, Z. Hossaini, Appl. Organomet. Chem. 35 (2021) e6193.

[27] E. Babaei, B. B. F. Mirjalili, Iran. J. Catal. 10 (2020) 219-226.

[28] A. Zare, N. Lotfifar, M. Dianat, J. Mol. Struct. 1211 (2020) 128030.

[29] Z. Kheilkordi, G. Mohammadi Ziarani, A. Badiei, H. Vojoudi, Iran. J. Catal. 10 (2020) 65-70.

[30] A. Zare, M. Barzegar, Res. Chem. Intermed. 46 (2020) 3727-3740.

[31] M. Himaja, D. Poppy, K. Asif, Int. J. Res. Ayurveda Pharm. 2 (2011) 1079-1086.

[32] Z. Abshirini, A. Kohzadian, Z. Paryav, A. Zare, Iran. J. Catal. 9 (2019) 251-257.

[33] F. Tamaddon, S. E. Tadayonfar, J. Mol. Liq. 280 (2019) 71-78.

[34] A. Zare, A. Kohzadian, Z. Abshirini, S. S. Sajadikhah, J. Phipps, M. Benamarad, M. H. Beyzavi, New J. Chem. 43 (2019) 2247-2257.

[35] J. H. Lee, H. B. Bang, S. Y. Han, J. G. Jun, Tetrahedron Lett. 48 (2007) 2889-2892.

[36] H. Zhao, N. Neamati, H. Hong, H. A. Mazumder, S. Wang, S. Sunder, G. W. A. Milne, Y. Pommier, T. R. Burke, J. Med. Chem. 40 (1997) 242-249.

[37] P. Anand, B. Singh, N. Singh, Bioorg. Med. Chem. 20 (2012) 1175-1180.

[38] A. A. Al-Amiery, A. A. H. Kadhum, A. B. Mohamad, Molecules 17 (2012) 5713-5723.

[39] H. Li, Y. Yao, L. Li, J. Pharm. Pharmacol. 69 (2017) 1253-1264.

[40] L. Z. Chen, W. W. Sun, L. Bo, J. Q. Wang, C. Xiu, W. J. Tang, J. B. Shi, H. P. Zhou, X. H. Liu, Eur. J. Med. Chem. 138 (2017) 170-181.

[41] I. Manolov, C. Maichle-Moessmer, I. Nicolova, N. Danchev, Arch. Pharm. 339 (2006) 319-326.

[42] K. M. Khan, S. Iqbal, M. A. Lodhi, G. M. Maharvi, Zia-Ullah, M. I. Choudhary, Atta-ur-Rahman, S. Perveen, Bioorg. Med. Chem. 12 (2004) 1963-1968.

[43] M. Choudhary, N. Fatima, K. M. Khan, S. Jalil, S. Iqbal, Atta-ur-Rahman, Bioorg. Med. Chem. 14 (2006) 8066-8072.

[44] N. Hamdi, M. C. Puerta, P. Valerga, Eur. J. Med. Chem. 43 (2008) 2541-2548.

[45] Q.-C. Ren, C. Gao, Z. Xu, L.-S. Feng, M.-L. Liu, X. Wu, F. Zhao, Curr. Top. Med. Chem. 18 (2018) 101-113. 

[46] B. M. Chougala, S. Samundeeswari, M. Holiyachi, N. S. Naik, L. A. Shastri, S. Dodamani, S. Jalalpure, S. R. Dixit, S. D. Joshi, V. A. Sunagar, Eur. J. Med. Chem. 143 (2018) 1744-1756.

[47] X. Jiang, M. Shangguan, Z. Lu, S. Yi, X. Zeng, Y. Zhang, L. Hou, Tetrahedron 76 (2020)  130921.

[48] C. Chen, L. Zhou, F. Liu, Z. Li, W. Liu, W. Liu, J. Hazard. Mater. 386 (2020) 121943.

[49] B. H. M. Hussein, G. M. Khairy, R. M. Kamel, Spectrochim. Acta A: Mol. Biomol. Spectrosc. 158 (2016) 34-42.

[50] H. Shahbazi-Alavi, A. K. Abbas, J. Safaei-Ghomi, Nanocomposites 6 (2020) 56-65.

[51] K. Parvanak Boroujeni, P. Ghasemi, Z. Rafienia, Monatsh. Chem. 145 (2014) 1023-1026.

[52] R. Teimuri-Mofrad, S. Tahmasebi, E. Payami, Appl. Organomet. Chem. 33 (2019) e4773.

[53] K. Parvanak Boroujeni, P. Ghasemi, Catal. Commun. 37 (2013) 50-54. 

[54] S. S. Kauthale, S. U. Tekale, K. M. Jadhav, R. P. Pawar, Mol. Divers. 20 (2016) 763-770.

[55] H. Bavandi, Z. Habibi, M. Yousefi, Bioorg. Chem. 103 (2020) 104139.

[56] B. Zeynizadeh, M. Sadeghbari, N. Noroozi Pesyan, J. Iran. Chem. Soc. 17 (2020) 73-88.

[57] N. Azizi, F. Abbasi, M. Abdoli-Senejani, ChemistrySelect 3 (2018) 3797-3802.

[58] E. Noroozizadeh, A. R. Moosavi-Zare, M. A. Zolfigol, M. Zarei, R. Karamian, M. Asadbegy, S. Yari, S. H. Moazzami Farida, J. Iran. Chem. Soc. 15 (2018) 471-481.

[59] H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7 (2010) 890-894.

[60] S. Qu, H. Yang, D. Ren, S. Kan, G. Zou, D. Liand, M. Li, J. Colloid Interf. Sci. 215 (1999) 190-192.

[61] M. A. Zolfigol, R. Ayazi-Nasrabadi, S. Baghery, Appl. Organomet. Chem. 30 (2016) 500-509. 

[62] Y. H. Deng, C. C. Wang, J. H. Hu, W. L. Yang, S. K. Fu, Colloids Surf. A 262 (2005) 87-93. 

[63] Y.-L. Hu, B.T. Wang, D. Fang, J. Iran. Chem. Soc. 14 (2017) 233-243.

[64] A. Alizadeh, M. Fakhari, M. M. Khodeai, G. Abdi, J. Amirian, RSC Adv. 7 (2017) 34972-34983.

[65] X. Pei, Y.H. Yan, L. Yan, P. Yang, J. Wang, R. Xu, M.B. Chan-Park, Carbon 48 (2010)   2501-2505.