Inorganic-organic hybrid nanomaterial (Fe3O4@SiO2-AQ): A retrievable heterogeneous catalyst for the green synthesis of 4H-chromenes
محورهای موضوعی : Iranian Journal of Catalysis
Mohamad Ali Bodaghifard
1
(Department of Chemistry, Faculty of Science, Arak University, Arak 38156-88138, Iran.|Institute of Nanosciences & Nanotechnology, Arak University, Arak, Iran.)
Zahra Faraki
2
(Department of Chemistry, Faculty of Science, Arak University, Arak 38156-88138, Iran.)
Zahra Mozaffari
3
(Department of Chemistry, Faculty of Science, Arak University, Arak 38156-88138, Iran.)
کلید واژه: Heterogeneous, 4H-chromenes, Green synthesis, Hybrid nanomaterial,
چکیده مقاله :
Preparation of 4-aminiquinaldine grafted on silica-coated nano-Fe3O4 particles (Fe3O4@SiO2-AQ) as a novel retrievable heterogeneous nanocatalyst is described. This novel hybrid nanomaterial was applicated for the green synthesis of substituted 2-amino-4H-chromenes via the one-pot condensation reaction of an aldehyde, malononitrile and α-naphthol/β-naphthol/phenol under solvent-free condition. Eco-friendly method, high yield and purity of the desired products, short reaction time along with the ease of the work-up procedure outlines the advantages of these new methodologies over the earlier ones. Surface and magnetic properties of the core/shell hybrid nanoparticles were characterized via transmission electron microscopy (TEM), scanning electron microscope (SEM), X-ray powder diffraction (XRD), energy-dispersive X-ray spectroscopy (EDS), thermogravimetric analysis (TGA/DTA), and Fourier-transform infrared spectroscopy (FT-IR) techniques. This nanocatalyst can be reused at least six times without considerable loss of its performance.
[1] J. Zhu, Q. Wang, M.-X. Wang, Multicomponent Reactions in Organic Synthesis. 1st Edition, Wiley-VCH, Weinheim, Germany, 2015.
[2] J. Zhu, H. Bienayme, Multicomponent Reactions. 1st Edition, Wiley-VCH, Weinheim, Germany, 2005.
[3] J. Montgomery, Acc. Chem. Res. 33 (2000) 467-473.
[4] H. Bienayme, K. Bouzid, Angew. Chem., Int. Ed. 37 (1998) 2234-2237.
[5] (a) R. V. Orru, M. de Greef, Synthesis 10 (2003) 1471-1499. (b) L. Chen, X.-J. Huang, Y.-Q. Li, W.-J. Zheng, Monatsh. Chem. 140 (2004) 45-47.
[6] L. F. Tietze, A. Modi, Med. Res. Rev. 20 (2000) 304-322. (b) S. J. Mohr, M. A. Chirigos, F. S. Fuhrman, J. W. Pryor, Cancer Res. 35 (1975) 3750-3754.
[7] A. Kakanejadifard, F. Azarbani, N. Khosravani, B. Notash, J. Mol. Liq. 221 (2016) 211-215.
[8] N. Seshu Babu, N. Pasha, K. T. Venkateswara Rao, P. S. Sai Prasad, N. Lingaiah, Tetrahedron Lett. 49 (2008) 2730-2733.
[9] S. Zavar, Arab. J. Chem. 10 (2017) S67.
[10] B. Wu, X. Gao, Z. Yan, M.‐W. Chen, Y.‐G. Zhou, Org. lett. 17 (2015) 6134-6137.
[11] G.‐D. Yin, T.‐T. Lai, Z.‐S. Yan, H. Chen, J. Zheng, Q. Tao, Tetrahedron 69 (2013) 2430-2435.
[12] G. Yin, H. Shi, L. Xu, X. Wei, Q. Tao, Synthesis 45 (2013) 334-340.
[13] A. F. Mahmoud, A. El‐Latif, F. Fathy, A. M. Ahmed, Chin. J. Chem. 28 (2010) 91-96.
[14] A. Shaabani, R. Ghadari, S. Ghasemi, M. Pedarpour, A. H. Rezayan, A. Sarvary, S. W. Ng, J. Comb. Chem. 11 (2009) 956-959.
[15] M. Fallah, Sh. Sohrabnezhad, M. Abedini, Appl. Organomet. Chem. 33 (2019) e4801.
[16] W. MA, A-Gh. Ebadi, M. shahbazi sabil, R. Javahershenas, G. Jimenez, RSC Adv. 9 (2019) 12801-12812.
[17] A. Poursattar Marjani, B. Ebrahimi Saatluo, F. Nouri, Iran. J. Chem. Chem. Eng. 37 (2018) 149-157.
[18] P. Gholamzadeh, G. M. Ziarani, N. Lashgari, A. Badiei, P. Asadiatouei, J. Mol. Catal. A: Chem. 391 (2014) 208-222.
[19] H. R. Shaterian, M. Mohammadnia, J. Mol. Liq. 177 (2013) 353-360.
[20] S. Thadkapally, A. C. Kunjachan, R. S. Menon, Beilstein J. Org. Chem. 12 (2016) 16-21.
[21] Ch. V. Subbareddy, Sh. Sumathi, New J. Chem. 41 (2017) 9388-9396.
[22] K. Kantharaju, S. Y. Khatavi, ChemistrySelect 3 (2018) 5016-5024.
[23] W. Injumpa, P. Ritprajak, N. Insin, J. Magn. Magn. Mater. 427 (2017) 60-66.
[24] S. H. Araghi, M. H. Entezari, Appl. Surf. Sci. 333 (2015) 68-77.
[25] M. A. Bodaghifard, M. Hamidinasab, N. Ahadi, Curr. Org. Chem. 22 (2018) 234-267.
[26] M. B. Gawande, P. S. Branco, R. S. Varma, Chem. Soc. Rev. 42 (2013) 3371-3393.
[27] J.A. Gladyzs, Chem. Rev. 102 (2002) 3215-3216.
[28] V. Polshettiwar, R. Luque, A. Fihri, H. Zhu, M. Bouhrara, J. M. Basset, Chem. Rev. 111 (2011) 3036-3075.
[29] S. Shylesh, V. Schünemann, W. R. Thiel, Angew. Chem. Int. Edit. 49 (2010) 3428-3459.
[30] Y. Leng, K. Sato, Y. Shi, J. G. Li, T. Ishigaki, T. Yoshida, H. Kamiya, J. Phys. Chem. C 113 (2009) 16681-16685.
[31] A. L. Morel, S. I. Nikitenko, K. Gionnet, A. Wattiaux, J. Lai-Kee-Him, C. Labrugere, B. Chevalier, G. Deleris, C. Petibois, A. Brisson, M. Simonoff, ACS Nano 2 (2008) 847-856.
[32] M. A. Bodaghifard, A. Mobinikhaledi, S. Asadbegi, Appl. Organometal. Chem. 31 (2017) e3557.
[33] M. A. Bodaghifard, S. Asadbegi, Z. Bahrami, J. Iran. Chem. Soc. 14 (2017) 365-376.
[34] M. A. Bodaghifard, A. Mobinikhaledi, M. Hamidinasab, Synth. React. Inorg. Met.-Org. Nano-Metal. Chem. 44 (2014) 567-571.
[35] K. Can, M. Ozmen, M. Ersoz, Colloids Surf. B Biointerfaces 71 (2009) 154-159.
[36] W. Stöber, A. Fink, E. Bohn, J. Colloid Interface Sci. 26 (1968) 62-69.
[37] (a) R. Sen, P. Jain, R. Patidar, S. Srivastava, R. Rana, N. Gupta, Mater. Today 2 (2015) 3750-3757. (b) M. K. Marchewka, Mat. Sci. Eng. B 95 (2002) 214-221. (c) M. Sarvestani, R. Azadi, Appl. Organometal. Chem. 31 (2017) e3667. (d) R. Nielsen, P. Kingshott, T. Uyar, J. Hacaloglu, K. L. Larsen, Surf. Interface Anal. 43 (2011) 884-892.
[38] G. Feng, D. Hu, L. Yang, Y. Cui, X.-A. Cui, H. Li, Sep. Purif. Technol. 74 (2010) 253-260.
[39] (a) J. Giri, S.G. Thakurta, J. Bellare, A. K. Nigam, D. Bahadur, J. Magn. Magn. Mater. 293 (2005) 62-68. (b) G. Alva, X. Huang, L. Liu, G. Fang, Appl. Energy 203 (2017) 677-685.
[40] K. Petcharoen, A. Sirivat, Mat. Sci. Eng. B 177 (2012) 421-427.
[41] S. M. Baghbanian, N. Rezaei, H. Tashakkorian, Green Chem. 15 (2013) 3446-3458.
[42] A. Kumbhar, S. Jadhav, R. Shejwal, G. Rashinkar, R. Salunkhe, RSC Adv. 6 (2016) 19612-19619.
[43] A. Mobinikhaledi, H. Moghanian, M. Ghanbari, Appl. Organometal. Chem. 32 (2018) e4108.
[44] T. S. Jin, J.C. Xiao, S. J. Wang, T. S. Li, Ultrason. Sonochem. 11 (2004) 393-397.
[45] T. S. Jin, J. S. Zhang, L. B. Liu, A. Q. Wang, T. S. Li, Synth. Commun. 36 (2006) 2009-2015.
[46] D. Kumar, V. B. Reddy, G. B. Mishra, R. K. Rana, M. N. Nadagouda, R. S. Varma, Tetrahedron 63 (2007) 3093-3097.
[47] H. Mehrabi, N. Kamali, J. Iran. Chem. Soc. 9 (2012) 599-605.
[48] H. Yan, J. Zhang, C. You, Z. Song, B. Yu, Y. Shen, Mater. Chem. Phys. 113 (2009) 46-52.
[49] R. Magar, P. Thorat, V. Jadhav, S. Tekale, S Dake, B. Patil, R. Pawar, J. Mol. Catal. A: Chem. 118 (2013) 374-375.
