Preparation, characterization and application of magnetic Fe3O4 @ CeO2 nanocatalysts for the synthesis of diindolyloxindole derivatives

Document Type : Original Article

Authors

Department of Chemistry, Faculty of Basic Sciences, Payam Noor University, Tehran

Abstract

Using hydrothermal method of reaction of Fe3O4 with cerium nitrate, magnetic nanoparticles of Fe3O4 @ CeO2 were prepared with average size 28-29 nm and detected by Fourier Transform Infrared Spectroscopy (FT-IR) and X-ray diffraction (XRD). The peak corresponding to each of the oxides was detectable in IR, and the successful synthesis of this nanocatalyst was confirmed by XRD. By studying the properties of nanocatalysts synthesized by vibrational sample magnetometry (VSM), its superparamagnetic properties were determined and its other properties were analyzed by scanning electron scanning electron microscopy (FE-SEM), X-ray diffraction (EDS) spectroscopy (X-ray diffraction spectroscopy). ) Checked out. The resulting shell – core structure of the nanocatalyst was fixed using XRD and EDS. Subsequently Fe3O4 @ CeO2 was used as an effective catalyst in the reaction of green synthesis of diindolyl oxindole derivatives from the coupling reaction between indole and isatin derivatives in the presence of water solvent. The reaction conditions in the presence of different catalysts were compared with the catalysts presented in this paper, which provided high speed and efficiency of this nanocatalyst. Easy separation (by external magnetic field), reusability in the reaction medium without significant loss of performance and non-toxicity are other advantages of this nanocatalyst.

Keywords

References

[1]. W. Zhang, Q. Zeng, X. Zhang, Y. Tian, Y. Yue, Y. Guo, Z. Wang, Org. Chem 76 (2011) 4741.
[2]. M. Shokouhimehr, Catalysts 5 (2015) 534.
[3]. E. K. Goharshadi, S. Samiee, and P. Nancarrow, J. Colloid Interface Sci. 356 (2011) 473.
[4]. D. Barreca, G. Bruno, A. Gasparotto, M. Losurdo, and E. Tondello, Mater. Sci. Eng. 23 (2003) 1013.
[5]. F. H. Garzon, R. Mukundan, and E. L. Brosha, Solid State Ionics 136 (2000) 633.
[6]. R. Di Monte, P. Fornasiero, M. Graziani, and J. Kaˇspar, J. Alloys Compd. 275 (1998) 877.
[7]. B. Elidrissi, M. Addou, M. Regragui, C. Monty, A. Bougrine, and A. Kachouane, Thin Solid Films 379 (2000) 23.
[8]. B. G. Wang, B.C. Ma, Q. Wang, W.Wang, Adv. Synth. Catal. 352 (2010) 2923.
[9]. O. Gleeson, R. Tekoriute, Y. K. Gunko, S. J. Connon, Chem. Eur. J. 15 (2009) 5669.
[10]. M. J. Jin, D. H. Lee, Angew. Chem. Int. Ed. 49 (2010) 1119.
[11]. H. Q. Yang, Y. Wang, Y. Qin, Y. Chong, Q. Yang, G. Li, L. Zhang, W. Li, Green Chem. 13 (2011) 1352.
[12]. G. Chouhan, D. Wang, H. Alper, Chem. Commun, (2007) 4809.
[13]. A. S. Singh, U. B. Patil, J. M. Nagarkar, Catal. Commun. 35 (2013) 1116.
[14]. C. W. Lim, I. S. Lee, Nano Today 5 (2010) 412.
[15]. M. Zhu, G. Diao, J. Phys. Chem. 115 (2011) 24743.
[16]. K. K. Senapati, S. Roy, C. Borgohain, P. J. Phukan, Mol. Catal. A: Chem. 352 (2012) 128.
[17]. P. Li, L. Wang, L. Zhang, G. W. Wang, Adv. Synth. Catal. 354 (2012) 1307.
[18]. R. S. Shelkar, S. H. Gund, J. M. Nagarkar, RSC Adv. 4 (2014) 53387.
[19]. A. S. Diez, M. G. Mayer, G. Radivoy, M. A. Volpe, Appl. Catal. A: Gen. 482 (2014) 24.
[20]. A. M. Akondi, R. Trivedi, B. Sreedhar, M. L. Kantam, S. Bhargava, Catal. Today 198 (2012) 3544.
[21]. S. M. Agawane, J. M. Nagarkar, Tetrahedron Lett. 52 (2011) 5220.
[22]. H. Hassani, M. Nasseri, B. Zakerinasab and F.Rafiee, Appl. Organomet. Chem. 30 (2016) 408.
[23]. B. Zakerinasab, M. Nasseri, H. Hassani and M.Samieadel, Res. Chem. Intermed. 42 (2016) 3169.
[24]. M. A. Nasseri, F. Ahrari and B. Zakerinasab, RSC Advances 5 (2015) 13901.
[25]. Z. Yang, Gh. Zhang, J. Zhang and W. Bai, Biosens. Bioelectron. (2014) 268
[26]. Sh. Xuant, Y. Xiang, J.C. Yu and K.Ch. Leung, Langmuir 25 (2009) 11835.
[27]. Y.Xiet, B.Yant, J.Chen. Y.Deng and H.Zeng, App.Mater.Interfaces, 6 (2014) 8845
[28]. R. S. Shelkara, K. E. Balsanea, J. M. Nagarkara, Tetrahedron Lett. 56 (2015) 693.
[29]. G. Neri, A. Pistone, C. Milone, S Galvagno, Appl. Catal. B. 38 (2002) 321.
[30]. J. Akhtara, N. S. Amina, A. Arisb, Chem. Eng. J. 170 (2011) 136
[31]. H. Bao, X. Chen, J. Fang, Z. Jiang, W. Huang, Catal. Lett. 125 (2008) 160.
[32]. G. K. Pradhan, K. M. Parida, Int. J. Eng. Sci. Technol. 2 (2010) 53.
[33]. Y. Kamimura, S. Sato; R. Takahashi, T. Sodesawa, T. Akashi, Appl. Catal. A: Gen 252 (2003) 399.
[34]. M. Nasseri, B. Zakerinasab and M. Samieadel, RSC Advances 4 (2014) 41753.
[35]. R. Bouhfied, N. Joly, F. Ohmani and E. Essassi, Lett.org.chem. 3 (2008).
[36]. S. N. Pandeya, D. Sriram, G. Nath and E, De clercq. Sci. Pharm. 67 (1999)103.
[37]. N. Terzioğlu, N. Karalı, A. Gürsoy, C. Pannecouque, P. Leysen, J. Paeshuyse, J. Neyts and E. De Clercq. Arkivoc (i) 109 (2006).
[38]. S. N. Pandeya, D. Sriram, G. Nath and E. De Clercq, Eur. J. Med. Chem. 35 (2000) 249.
[39]. A. E. Wright, S. A. Pomponi, S. S. Ctross, McCarthy, P. J. J Org Chem, 57 (1992) 4772.
[40]. J. E. M. N. Klein, R. J. K. Taylor, Eur. J. Org. Chem. 34 (2011) 6821.
[41]. T. H. Kang, Y. Murakami, K. Matsumoto, H. Takayama, M. Kitajima, N. Aimi, H. Watanabe, Eur. J. Pharmacol. 455 (2002) 27.
[42]. A. M. Swensen, J. Herrington, R. M. Bugianesi, G. Dai, R. J. Haedo, K. S. Ratliff, M. M. Smith, V. A. Warren, S. P. Arneric, C. Eduljee, D. Parker, T. P. Snutch, S. B. Hoyt, C. London, J. L. Duffy, G. J. Kaczorowski, O. B. McManus, Mol. Pharmacol. 81 (2012) 488.
[43]. J. L. Whatmore, E. Swann, P. Barraja, J. J. Newsome, M. Bunderson, H. D. Beall, J. E. Tooke C. Moody, J. Angiogenesis 5 (2002) 45.
[44]. S. Peddibhotla Curr. Bioactive Compd, 5 (2009) 20.
[45]. C. Abbadie, O. B. McManus, S. Y. Sun, R. M. Bugianesi, G. Dai, R. J. Haedo, J. B. Herrington, G. J. Kaczorowski, M. M. Smith, A. M. Swensen, V. A. Warren, B. Williams, S. P. Arneric, C. Eduljee, T. P. Snutch, E. W. Tringham, N. Jochnowitz, A. Liang, D. Euan MacIntyre, E. McGowan, S. Mistry, V. V. White, S. B. Hoyt, C. London, K. A. Lyons, P. B. Bunting, S. Volksdorf, J. L. Duffy, J. Pharmacol. Exp. Ther. 334 (2010) 545.
[46]. S.S. Pourpanah, S.M. Habibi-Khorassani, M. Shahraki, Chin. J. Catal. 36 (2015) 757.
[47]. F.N. Sadeh, M.T. Maghsoodlou, N. Hazeri, M. Kangani, Res. Chem. Intermed. 41 (2015) 5907.
[48]. Y.B. Wagh, Y.A. Tayade, S.A. Padvi, B.S. Patil, N.B. Patil, D.S. Dalal, Chin. Chem. Lett. 26 (2015) 127
[49]. M.A. Nasseri, B. Zakerinasab, M. Samieadel, RSC Adv. 79 (2014) 41753.
[50]. Zakerinasab, M. A. Nasseri, H. Hassani, M. Samieadel, Res. Chem. Intermed. 42 (2016) 3169.
[51]. R. C. Martins, N. Amaral-Silva, R. M. Quinta-Ferreira, Appl. Catal, B 99 (2010) 135.
[52]. I. Karimzadeh, M. Aghazadeh, T. Doroudi, M.R. Ganjali, P. H. Kolivand. Adv. Phys. Chem. 2017 (2017) 1.
[53]. M. Farahmandjou, M. Zarinkamar. J. Ultrafine Grained Nanostruct. Mater. 48 (2015) 5.
[54]. M. K. Trivedi, A. Branton, D. Trivedi, G. Nayak, K. Bairwa, S. Jana. J. Chromatogr. Sep. Tech. 6 (2015).
[55]. K. S. Loh, Y. H. Lee, A. A. Musa, Z. Ishak. Sensors. 8 (2008) 5775.
[56]. S. J. Iyengar, M. Joy, C. K. Ghosh, S. Dey, R. K. Kotnala, S. Ghosh. RSC Adv. 4 (2014) 64919.
[57]. G. Jayakumar, A. Albert Irudayaraj, A. Dhayal Raj. MMSE Journal. (2017).
[58]. Y. H. Zhou, Z. Zhang, S. Wang, N. Williams, Y. Cheng, S. Luo, J. Gu. Int. J. Hydrogen Energy. 43 (2018) 18745.
[59]. Q. Q. Zhu, L. X. Zhong, L. X. Yang, X. Xu. ECS J. Solid State Sci. Technol. 1 (2012) 119.
[60]. V. Alimohammadi, F. Kashanian, S. A. Seyyed Ebrahimi, M. Habibi Rezaei, A. Bagherpour. Metall. Eng. 21 (2019) 275, (in persian).
[61]. H. Asnaashar, H. Arabi, Nanomatherials 8 (2016) 11, (in persian).
[62]. V. Kandathil, B. D. Fahlman, B. S. Sasidhar, S. A. Patil, S. A. Patil. New J. Chem. 41 (2017) 9531.
[63]. B.V. Subbareddy, N. Rajeswari, Y. Prashanthi, R.J. Ganji and A. Addlagatla, Bioorg. Med. Chem. Lett. 22 (2012) 2460.
[64]. A. Kamal, Y. V. V. Srikanth, M. Naseer A. Khan, T. Basha Shaik and Md. Ashraf, Bioorg. Med. Chem. Lett. 20 (2010) 5229.
[65]. A. R. Khorshidi, k. Tabatabaeian, Ori. J. Chem. 26 (2010) 837.
[66]. K. Nikoofar, M. Hanhighi and Z. Khademi, Arabian J. Chem. (2016).
[67]. M. A. Nasseri, B. Zakerinasab, Iranian JOC 5 (2013) 109.
Applied Chemistry Today
Volume 16, Issue 58
April 2021
Pages 149-166

Files

Share

How to cite

Statistics