Imidazolium Hydrogen Sulphate Supported on Copper Oxide Nanoparticles as an efficient simple Heterogeneous Acidic Catalyst for Multi-component Synthesis of 1, 4- dihydro Pyrano [2, 3-c] pyrazoles Derivatives
الموضوعات : Iranian Journal of Catalysis
Elham Fadavipoor
1
(Department of Chemistry, Sousangerd Branch, Islamic Azad University, Sousangerd, Iran)
Rashid Badri
2
(Department of Chemistry, College of Science, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran)
الکلمات المفتاحية: Multi-component reactions, Functionalize, CuO NPs, Imidazolium,
ملخص المقالة :
Si-Im/HSO4(1-methyl-3-(3-(trimethoxysilyl) propyl) imidazolium hydrogen sulphate functionalized Copper oxide nanoparticles(CuO NPs )as a novel supporting ionic liquid was prepared and characterized by FT-IR spectroscopy, FE-SEM, XRD, TGA, and EDX techniques. It was used as a recyclable catalyst for the one-pot, three-component synthesis of 1, 4- dihydro Pyrano [2, 3-c] pyrazoles derivatives. The results showed that the catalyst was very efficient, and in addition, at the end of the reaction the catalyst could be easily isolated and reused for the next reaction without any appreciable loss of its catalytic activity. The reused catalyst was also characterized by the FE-SEM and EDX techniques.
[1] K. Singh, J. singh, H. Singh, Tetrahedron. 52 (1996) 14273-14280.
[2] L. Khazdooz, A. zarei, Iran. J. Catal. 6 (2016) 69-74.
[3] P. T. Mistry, N. R. Kamdar, D. D. Haveliwala, S. K. Patel, J. Heterocycl. Chem. 4 (2012) 349-357.
[4] F. Rigi, H. R. Shaterian, J. Polycyclic. Arom. Compound. 37 (2017) 314-326.
[5] H. Wamhoff, E. Korth, C. Strauch, Synth. 11 (1993)1129-1132.
[6] M. Beerappa, K. Shivashankar, J. Synth. Commun. 48 (2018) 146-154.
[7] Z. Hajizadeh, A. Maleki, Mol. Catal. 460 (2018) 87-93.
[8] M. Babaie, H.Sheibani, Arabia. J. Chem. (2011) 159-162.
[9] V. E. Henrich, P. A. Cox-1996-480 pages, “The surface science of metal oxides”. 1996.
[10] J. Albadi, A. Razeghi, A. Mansournezhad, Z. Azarian, J. Nanostructure.Chem. 3 (1) (2013) 1-5.
[11] A. R. Kiasat, S. Nazari, Catal. Commun, 18 (2012) 102-105.
[12] M. F. García, A. M. Arias, J. C. Hanson, Chem. Rev. 104 (2004) 4063-4104.
[13] C. Siriwong, P. Sae-Oui, C. Sirisinha, Polym. Test. 38 (2014) 64-72.
[14] S. Nazari, S. Saadat, P. Kazemianfard, M. Gorjizadeh, E. Rezaeenezhad, M. Afshari, Monatsh. Chem. 144 (2013) 1877-1882.
[15] M. A. Zolfigol, A. Khazaei, A. R. Moosavi-Zare, A. Zare, Org. Pre. Procedure. Int. 42 (2010) 95-102.
[16] M. E. Gonzalez- Núñez, R. Mello, A. Olmos, G. Asensio, J. Org. Chem. 70 (2005) 10879-10882.
[17] E. Smith, A. P. Abbott, K. S. Ryder, Chem. Rev. 114 (2014) 11060-11082.
[18] L. Z. Juan, Z. Feng, X. Liang, X. Hua, L. Xia, J. S. Xiang, Chem. Lett. 33 (2004) 496-497.
[19] T. Selvam, A. Machoke, W. Schwieger, Appl. Catal A: Gen. 455-456 (2012) 92-101.
[20] J. Davarpanah, R. Khoram, J. Nanoanalysis. 4 (2017) 20-30.
[21] J. Miao, H. Wan, Y. Shao, G. Guan, B. Xu, J. Mol. Catal A: Chem. 348 (2011) 77-82.
[22] K. Qiao, H. Hagiwara, C. Yokoyama, J. Mol. Catal A: Chem. 246 (2006) 65-69.
[23] A. Chrobok, S. Baj, W. P. Jarzebski, Appl. Catal A: Gen. 366 (2009) 22-28.
[24] M. Nourisefat, D. Saberi, K. Niknam, Catal. Lett. 141 (2011) 1713-1720.
[25] M. Baghernejad, K. Niknam, Int. J. Chem. 4 (2012) 52-60.
[26] K. Niknam, A. Piran, Z. Karimi, J. Iran. Chem. Soc. 13 (2016) 859-871.
[27] L. Rout, T. K. Sen, T. Punniyamurthy, Org. Lett. 9 (2007) 5583-5586.
[28] L. Rout, S. Jammi, T. Punniyamurthy, Org. Lett. 9 (2007) 3397-3399.
[29] M. Nasrollahzadeh, M. Maham, M. Sajadi, J. Coll. Inter Science. 455 (2015) 245-253.
[30] P. Moradi, M. Hajjami, New. J. Chem. 45 (2021) 2981-2994.
[31]A. Ghorbani-Choghamarani, M. A. Zolfigol, Z. M. Hajjami, H. H. Goudarziafshar, M. Nikoorazm, S. Yousefi, B. Tahmasbi, J. Braz. Chem. Soc. 22 ( 3) (2011) 525-531.
[32] A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, Polyhedron. 163 (2019) 98-107.
[33] P. Moradi, M. Hajjami, B. Tahmasbi. 175 (2020) 114169.
[34] A. A. Ghorbani-Choghamarani, Z. Seydyosefi, B. Tahmasbi, C. R. Chimie, 21(11) (2018) 1011-1022.
[35] B. Tahmasbi, A. Ghorbani-Choghamarani, P. Moradi, N. J. Chem. 44 (9) (2020) 3717-3727.
[36] B. Atashkar, A. Rostami, H. Gholami, B. Tahmasbi, Res Chem Intermed. 41 (2015) 3675–3681.
[37] A. Ghorbani-Choghamarani, P. Moradi, B. Tahmasbi, J. Iran. Chem. Soc. 16 (2019) 511–521.
[38] M. Nikoorazm, Z. Rezaei, B. Tahmasbi, J. Porous Mater. 27 (2020) 671–689.
[39] M. Nourisefat, D. Saberi, K. Niknam, Catal. Lett. 141 (2011) 1713-1720.
[40] M. Saha, A. Kumarpal, Advances in Nanopart. 1 (2012) 61-70.
[41] E. Fadovipoor, S. Nazari, A. Zarei Ahmady, M. Afshari, M. Keshavarz, Orient. J. Chem. 31 (2015) 733-739.
[42] T. S. Jin, R. Q. Zhao, T. S. Li, Arkivoc. (2006) 176-182.
[43] H. Valizadeh, M. Amiri, F. Hosseinzadeh, Dyes. Pig. 92 (2012) 1308-1313.
[44] M. Nikoorazm, B. Tahmasbi, S. Gholami, P. Moradi, Appl Organomet Chem. 34(11) (2020) e5919.
