Ecofriendly synthesis of biscoumarin derivatives catalyzed by EDTA-modified magnetic animal bone meal nanoparticles in water
محورهای موضوعی : Iranian Journal of CatalysisAhmad Reza Momeni 1 , Sadegh Bakhtiar 2
1 - Faculty of Sciences, Shahrekord University, Shahrekord, Iran.
2 - Faculty of Sciences, Shahrekord University, Shahrekord, Iran.
کلید واژه: Biscoumarin, Green catalyst, Animal bone meal, Ethylenediaminetetraacetic acid, Magnetic nanoparticels,
چکیده مقاله :
In this research, magnetic animal bone meal nanoparticles functionalized with ethylenediaminetetraacetic acid (Fe3O4@ABM-EDTA) is reported as a green recyclable catalyst that catalyzed synthesis of biscoumarin derivatives in water. The catalyst was characterized by the Fourier transform infrared spectroscopy (FT-IR), thermogravimetric analysis (TGA), differential thermogravimetric (DTG), scanning electron microscope (SEM) and X-ray diffraction (XRD). This study has demonstrated that Fe3O4@ABM-EDTA can act as an efficient catalyst for synthesis of biscoumarines in the presence of water as solvent at reflux conditions. A wide range of aldehydes could react with 2-hydroxycoumarin and give biscoumarin derivatives in excellent yields. Moreover, Fe3O4@ABM-EDTA was magnetically recovered and reused for five cycles without any significant loss of efficiency.
[1] P.T. Anastas, J.C. Warner, Green chemistry: theory and practice, Oxford University Press, 2000.
[2] P.T. Anastas, L.B. Bartlett, M.M. Kirchhoff, T.C. Williamson, Catal. Today 55 (2000) 11-22.
[3] B. Dam, S. Nandi, A.K. Pal, Tetrahedron Lett. 55 (2014) 5236-5240.
[4] R. Ghahremanzadeh, Z. Rashid, A.H. Zarnani, H. Naeimi, App. Catal. A 467 (2013) 270-278.
[5] P.K. Saikia, P.P. Sarmah, B.J. Borah, L. Saikia, K. Saikia, D.K. Dutta, Green Chem. 18 (2016) 2843-2850.
[6] Y. Riadi, R. Mamouni, R. Azzalou, R. Boulahjar, Y. Abrouki, M. El Haddad, S. Routier, G. Guillaumet, S. Lazar, Tetrahedron Lett. 51 (2010) 6715-6717.
[7] M. Sillanpää, M. Orama, J. Rämö, A. Oikari, Sci. Total Environ. 267 (2001) 23-31.
[8] E. Repo, T.A. Kurniawan, J.K. Warchol, M.E. Sillanpää, J. Hazard. Mater. 171 (2009) 1071-1080.
[9] E. Repo, J.K. Warchol, T.A. Kurniawan, M.E. Sillanpää, Chem. Eng. J. 161 (2010) 73-82.
[10] L. Wang, L. Yang, Y. Li, Y. Zhang, X. Ma, Z. Ye, Chem. Eng. J. 163 (2010) 364-372.
[11] O.K. Júnior, L.V.A. Gurgel, R.P. de Freitas, L.F. Gil, Carbohyd. Poly. 77 (2009) 643-650.
[12] D.N. Korolev, N.A. Bumagin, Tetrahedron Lett. 46 (2005) 5751-5754.
[13] F. Li, Y. Li, J. Mol. Catal. A: Chem. 420 (2016) 254-263.
[14] J. Ma, L. Zhong, X. Peng, R. Sun, Green Chem. 18 (2016) 1738-1750.
[15] K.M. Khan, S. Iqbal, M.A. Lodhi, G.M. Maharvi, M.I. Choudhary, S. Perveen, Bioorg. Med. Chem. 12 (2004) 1963-1968.
[16] R.D.R. Manian, J. Jayashankaran, R. Raghunathan, Tetrahedron Lett. 48 (2007) 1385-1389.
[17] I. Manolov, C. Maichle‐Moessmer, I. Nicolova, N. Danchev, Arch. Pharm. 339 (2006) 319-326.
[18] J. Lehmann, Lancet 241 (1943) 611-613.
[19] M.A. Zolfigol, A.R. Moosavi-Zare, M. Zarei, C.R. Chim. 17 (2014) 1264-1267.
[20] R. Rezaei, F. Moezzi, M.M. Doroodmand, Chin. Chem. Lett. 25 (2014) 183-186.
[21] K.P. Boroujeni, P. Ghasemi, Z. Rafienia, Monat. Chem. 145 (2014) 1023-1026.
[22] H. Mehrabi, H. Abusaidi, J. Iran. Chem. Soc. 7 (2010) 890-894.
[23] K. Niknam, S.A. Sajadi, R. Hosseini, M. Baghernejad, Iran. J. Catal. 4 (2014) 163-173.
[24] K.M. Khan, F. Rahim, A. Wadood, N. Kosar, M. Taha, S. Lalani, A. Khan, M.I. Fakhri, M. Junaid, W. Rehman, Eur. J. Med. Chem. 81 (2014) 245-252.
[25] 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.
[26] K. Tabatabaeian, H. Heidari, A. Khorshidi, M. Mamaghani, N.O. Mahmoodi, J. Serb. Chem. Soc. 77 (2012) 407-413.
[27] E. Noroozizadeh, A.R. Moosavi-Zare, M.A. Zolfigol, M. Zarei, R. Karamian, M. Asadbegy, S. Yari, S.H.M. Farida, J. Iran. Chem. Soc. 15 (2018) 471-481.
[28] A. Sahar, Z.A. Khan, M. Ahmad, A.F. Zahoor, A. Mansha, A. Iqbal, Trop. J. Pharm. Res. 16 (2017) 203-210.
[29] J. Safari, Z. Zarnegar, J.Mol. Catal. A: Chem. 379 (2013) 269-276.
[30] M. Tuelue, K.E. Geckeler, Polym. Int. 48 (1999) 909-914.
[31] Y. Shiraishi, G. Nishimura, T. Hirai, I. Komasawa, Ind. Eng. Chem. Res. 41 (2002) 5065-5070.
[32] M. Tahriri, M. Solati-Hashjin, H. Eslami, Iran. J. Pharm. Sci. 4 (2008) 127-134.
[33] Y. Ren, H.A. Abbood, F. He, H. Peng, K. Huang, Chem. Eng. J. 226 (2013) 300-311.
[34] K. Azizi, M. Karimi, F. Nikbakht, A. Heydari, App. Catal. A 482 (2014) 336-343.
