Novel nanomagnetic material with dimethylamino tag: a selective and recyclable catalyst for the reaction of malononitrile, aryl aldehydes and dimedone
الموضوعات : Iranian Journal of CatalysisAysoda Ghobadpoor 1 , Mohammad Mehdi Eskandari 2 , Abdolkarim Zare 3 , Mostafa Karami 4
1 - Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran.
2 - Nanotechnology Research Center, Research Institute of Petroleum Industry (RIPI), PO Box 1485733111, Tehran, Iran.
3 - Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran.
4 - Department of Chemistry, Payame Noor University, PO Box 19395-3697, Tehran, Iran.
الکلمات المفتاحية: Multi-component reaction, Nanomagnetic catalyst, Nano-Fe3O4@SiO2@R-NMe2 ([NFSRN]), 2-Amino-tetrahydrobenzo[b]pyran,
ملخص المقالة :
A novel nanomagnetic material with a dimethylamino tag namely nano-Fe3O4@SiO2@R-NMe2 ([NFSRN]) was produced, and characterized by EDS, FT-IR, VSM, FE-SEM, XRD and TGA analyses. Then, it was applied as a highly effective and magnetically recyclable catalyst for the one-pot multi-component reaction of malononitrile, arylaldehydes and dimedone. Interestingly, in most entries, among the possible products which can be produced from the reactants, only 2-amino-tetrahydrobenzo[b]pyrans were obtained in high yields and relatively short times, and no other product was obtained.
[1] Y. Wei, B. Han, X. Hu, Y. Lin, X. Wang, X. Deng, Procedia Eng. 27 (2012) 632-637.
[2] J. Sun, S. Zhou, P. Hou, Y. Yang, J. Weng, X. Li, M. Li, J. Biomed. Mater. Res. A 80 (2007) 333-341.
[3] M. Ahmadi, H. Elmongy, T. Madrakian, M. Abdel-Rehim, Anal. Chim. Acta 958 (2017) 1-21.
[4] H.-p. Feng, L. Tang, G.-m. Zeng, Y. Zhou, Y.-c. Deng, X. Ren, B. Song, C. Liang, M.-y. Wei, J.-f. Yu, Adv. Colloid Interface Sci. 267 (2019) 26-46.
[5] B. K. Purushothaman, M. Harsha S, P. U. Maheswari, K. M. M. S. Begum, J. Drug Deliv. Sci. Technol. 52 (2019) 509-520.
[6] A. Majouga, M. Sokolsky-Papkov, A. Kuznetsov, D. Lebedev, M. Efremova, E. Beloglazkina, P. Rudakovskaya, M. Veselov, N. Zyk, Y. Golovin, N. Klyachko, A. Kabanov, Colloids Surf. B: Biointerfaces 125 (2015) 104-109.
[7] R. S. García, S. Stafford, Y. K. Gunʹko, Appl. Sci. 8 (2018) 172.
[8] C. Pereira, R. S. Costa, L. Lopes, B. Bachiller-Baeza, I. Rodríguez-Ramos, A. Guerrero-Ruiz, P. B. Tavares, C. Freire, A. M. Pereira, Nanoscale 10 (2018) 12820-12840.
[9] J. Kothandapani, S. S. Ganesan, Curr. Org. Chem. 23 (2019) 313-334.
[10] F. Tamaddon, D. Arab, E. Ahmadi-AhmadAbadi, Carbohydr. Polym. 229 (2020) 115471.
[11] B. B. F. Mirjalili, R. Araqia, S. A. Mohajeri, Iran. J. Catal. 9 (2019) 11-19.
[12] R. Kordnezhadian, M. Shekouhy, A. Khalafi-Nezhad, New J. Chem. 43 (2019) 18559-18570.
[13] M. M. Dutta, H. Talukdar, P. Phukan, Dalton Trans. 48 (2019) 16041-16052.
[14] Z. Kheilkordi, G. Mohammadi Ziarani, A. Badiei, H. Vojoudi, Iran. J. Catal. 10 (2020) 65-70.
[15] M. Torabi, M. Yarie, M. A. Zolfigol, Appl. Organomet. Chem. 33 (2019) e4933.
[16] H. R. Safaei, T. Khastkhoda, M. Shekouhy, ChemistrySelect 3 (2018) 6273-6278.
[17] Z. Abshirini, A. Kohzadian, Z. paryav, A. Zare, Iran. J. Catal. 9 (2019) 251-257.
[18] A. Zare, A. Kohzadian, Z. Abshirini, S. S. Sajadikhah, J. Phipps, M. Benamarad, M. H. Beyzavi, New J. Chem. 43 (2019) 2247-2257.
[19] A. Kakavand Ghalenoei, M. Bakherad, A. Keivanloo, Iran. J. Catal. 9 (2019) 293-303.
[20] F. W. Perrella, S. F. Chen, D. L. Behrens, R. F. Kaltenbach, S. P. Seitz, J. Med. Chem. 37 (1994) 2232-2237.
[21] Y. Wang, S.-Y. Mo, S.-J. Wang, S. Li, Y.-C. Yang, J.-G. Shi, Org. Lett. 7 (2005) 1675-1678.
[22] R. Schiller, L. Tichotová, J. Pavlík, V. Buchta, B. Melichar, I. Votruba, J. Kuneš, M. Špulák, M. Pour, Bioorg. Med. Chem. Lett. 20 (2010) 7358-7360.
[23] H. Hussain, S. Aziz, B. Schulz, K. Krohn, Nat. Prod. Commun. 6 (2011) 841-843.
[24] R. R. Kumar, S. Perumal, P. Senthilkumar, P. Yogeeswari, D. Sriram, Bioorg. Med. Chem. Lett. 17 (2007) 6459-6462.
[25] L. Bonsignore, G. Loy, D. Secci, A. Calignano, Eur. J. Med. Chem. 28 (1993) 517-520.
[26] G. Sabitha, K. Arundhathi, K. Sudhakar, B. S. Sastry, J. S. Yadav, Synth. Comm. 39 (2009) 433-442.
[27] G. P. Ellis, The Chemistry of Heterocyclic Compounds, Chromenes, Chromanes and Chromones; A. Weissberger, E. C. Taylor (Eds.); John Wiley: New York, NY, USA (1977), pp. 11-139.
[28] D. Armetso, W. M. Horspool, N. Martin, A. Ramos, C. Seoane, J. Org. Chem. 54 (1989) 3069-3072.
[29] H. R. Saadati-Moshtaghin, F. Mohammadi Zonoz, Res. Chem. Intermed. 44 (2018) 2195-2213.
[30] L. Khazdooz, A. Zarei, T. Ahmadi, H. Aghaei, L. Golestanifar, N. Sheikhan, Res. Chem. Intermed. 44 (2018) 93-115.
[31] F. Ataiea, A. Davoodnia, A. Khojastehnezhad, Polycycl. Aromat. Compd., in press, doi: 10.1080/10406638.2019.1622137.
[32] M. Hajjami, F. Gholamian, R. H. E. Hudson, A. M. Sanati, Catal. Lett. 149 (2019) 228-247.
[33] S. Nemouchi, R. Boulcina, B. Carboni, A. Debache, C. R. Chim. 15 (2012) 394-397.
[34] H. Hu, F. Qiu, A. Ying, J. Yang, H. Meng, Int. J. Mol. Sci. 15 (2014) 6897-6909.
[35] S. Rostamnia, A. Morsali, Inorg. Chim. Acta 411 (2014) 113-118.
[36] M. Shahabi Nejad, H. Sheibani, Catal. Lett. 148 (2018) 125-133.
[37] M. Esmaeilpour, J. Javidi, F. Dehghani, F. Nowroozi Dodeji, RSC Adv. 5 (2015) 26625-26633.
[38] S. Qu, H. Yang, D. Ren, S. Kan, G. Zou, D. Liand, M. Li, J. Colloid Interface Sci. 215 (1999) 190-192.
[39] M. A. Zolfigol, R. Ayazi-Nasrabadi, S. Baghery, Appl. Organomet. Chem. 30 (2016) 273-281.
[40] Y. H. Deng, C. C. Wang, J. H. Hu, W. L. Yang, S. K. Fu, Colloids Surf. A 262 (2005) 87-93.
[41] A. Zare, R. Khanivar, N. Irannejad-Gheshlaghchaei, M. H. Beyzavi, ChemistrySelect 4 (2019) 3953-3960.
[42] A. Zanon, S. Chaemchuen, F. Verpoort, Catal. Lett. 147 (2017) 2410-2420.
[43] B. Zeynizadeh, S. Rahimi, A. Hallaj, Curr. Org. Synth. 16 (2019) 939-947.
[44] M. Nasr-Esfahani, T. Abdizadeh, J. Nanosci. Nanotechnol. 13 (2013) 5004-5011.