Tungstophosphoric acid embedded magnetic chitosan as a green catalyst for the synthesis of N-cyclohexyl-3-aryl quinoxaline-2-amines
الموضوعات : Iranian Journal of Catalysis
Ali Ayati
1
(Department of Chemical Engineering, Quchan University of Advanced Technology, Quchan, Iran.)
Mansoureh Daraie
2
(Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran.)
Majid Heravi
3
(Department of Chemistry, School of Sciences, Alzahra University, Vanak, Tehran, Iran.)
Bahareh Tanhaei
4
(Department of Chemical Engineering, Quchan University of Advanced Technology, Quchan, Iran.)
الکلمات المفتاحية: Green synthesis, Heteropolyacid, Multicomponent reactions, Magnetic Chitosan,
ملخص المقالة :
In the present study, a novel catalyst was well designed by incorporating the tungstophosphoric acid into the magnetic chitosan, as highly stable composite, in which the iron oxides were used the strong super-magnetic core. The prepared composite was characterized by several methods, including FTIR, XRD, SEM, TEM and EDS and its catalytic activity was examined in a facile, green and highly efficient one-pot reaction for the synthesis of N-cyclohexyl-3-aryl-quinoxaline-2-amines with o-phenylenediamine, benzaldehyde and cyclohexyl isocyanide in water, under reflux conditions. This heterogeneous catalytic system was separated easily by an external magnet and was reused at least in four runs without pre-activation and appreciable loss in its activity.
[1] M.M. Heravi, G. Rajabzadeh, F.F. Bamoharram, N. Seifi, J. Mol. Catal. A: Chem. 256 (2006) 238-241.
[2] A. Ayati, A. Ahmadpour, F.F. Bamoharram, M.M. Heravi, H. Rashidi, Chin. J. Catal. 32 (2011) 978-982.
[3] M.M. Heravi, V. Zadsirjan, K. Bakhtiari, H.A. Oskooie, F.F. Bamoharram, Catal. Commun. 8 (2007) 315-318.
[4] F.F. Bamoharram, M.M. Heravi, S. Mehdizadeh, Synth. React. Inorg. Met.-Org. Nano-Met. Chem. 39 (2009) 746-750.
[5] A. Ayati, A. Ahmadpour, F.F. Bamoharram, M.M. Heravi, M. Sillanpää, Gold Bull. 45 (2012) 145-151.
[6] M.M. Heravi, S. Sadjadi, J. Iran. Chem. Soc. 6 (2009) 1-54.
[7] S. Sadjadi, M.M. Heravi, Curr. Org. Chem. 20 (2016) 1404-1444.
[8] M.M. Heravi, H. Alinejhad, K. Bakhtiari, Z. Daroogheha, F.F. Bamoharram, F. Derikvand, B. Alimadadi, Synthetic Communications 40 (2010) 2191-2200.
[9] M.M. Heravi, E. Hashemi, Y.S. Beheshtiha, K. Kamjou, M. Toolabi, N. Hosseintash, J. Mol. Catal. A: Chem. 392 (2014) 173-180.
[10] L.T.A. Sofia, A. Krishnan, M. Sankar, N.K.K. Raj, P. Manikandan, P.R. Rajamohanan, T.G. Ajithkumar, J. Phys Chem. C 113 (2009) 21114-21122.
[11] M.M. Heravi, V. Rasmi, F.F. Bamoharram, S. Sadjadi, L. Fotouhi, S. Sadjadi, M. Bakavoli, Synth. Commun. 39 (2009) 4109-4116.
[12] A. Micek-Ilnicka, E. Bielanska, L. Litynska-Dobrzynska, A. Bielanski, Appl. Catal. A 421- 422 (2012) 91- 98.
[13] N. Toutounchian, A. Ahmadpour, M.M. Heravi, F.F. Bamoharram, A. Ayati, F. Deymeh, Res. Chem. Intermed. 42 (2016) 3283-3301.
[14] T. Alishiri, H.A. Oskooei, M.M. Heravi, Synt. Commun. 43 (2013) 3357-3362.
[15] F. Nemati, M.M. Heravi, A. Elhampour, RSC Adv. 5 (2015) 45775-45784.
[16] M. Feyen, C. Weidenthaler, F. Schüth, A.H. Lu, Chem. Mater. 22 (2010) 2955-2961.
[17] J. Safari, L. Javadian, Ultrason. Sonochem. 22 (2015) 341-348.
[18] A. Naghipour, A. Fakhri, Catal. Commun. 73 (2016) 39-45.
[19] M. Bodnar, J.F. Hartmann, J. Borbely, Biomacromolecule 6 (2005) 2521-2527.
[20] W. Li, L. Xiao, C. Qin, J. Macromol. Sci. A Pure. Appl. Chem. 48 (2010) 57-64.
[21] B. Tanhaei, A. Ayati, M. Lahtinen, M. Sillanpää, Chem. Eng. J. 259 (2015) 1-10.
[22] A. Ayati, B. Tanhaei, M. Sillanpää, J. Appl. Polym. Sci. 134 (2017) 44360.
[23] A. Ayati, M.M. Heravi, M. Daraie, B. Tanhaei, F.F. Bamoharram, M. Sillanpää, J. Iran Chem. Soc. 13 (2016) 2301–2308.
[24] A. Kong, P. Wang, H. Zhang, F. Yang, S.P. Huang, Y. Shan, App. Phys. A: Gen. 417- 418 (2012) 183-189.
[25] H.E. Blackwell, Curr. Opin. Chem. Biol. 10 (2006) 203-212.
[26] B.B. Toure, D.G. Hall, Chem. Rev. 109 (2009) 4439-4486.
[27] M.M. Heravi, B. Talaei, Adv. Heterocycl. Chem. 114 (2015) 147-225.
[28] S. Brauch, S.S.v. Berkel, B. Westermann, Chem. Soc. Rev. 42 (2013) 4948-4962.
[29] A. Domling, Chem. Rev. 106 (2006) 17-89.
[30] S. Sadjadi, M.M. Heravi, Tetahedron 67 (2011) 2707-2752.
[31] K. Toshima, R. Takano, T. Ozawa, S. Matsumura, Chem. Commun. 3 (2002) 212-213
[32] F. Zaragoza, H. Stephensen, J. Org. Chem. 64 (1999) 2555-2557.
[33] S.A. Raw, C.D. Wilfred, R.J.K. Taylor, Chem. Commun. 18 (2003) 2286-2287.
[34] K.R.J. Thomas, M. Velusamy, J.T. Lin, C.-H. Chuen, Y.-T. Tao, Chem. Mater. 17 (2005) 1860-1866.
[35] S. Dailey, W.J. Feast, R.J. Peace, I.C. Sage, S. Till, E.L. Wood, J. Mater. Chem. 11 (2001) 2238-2243.
[36] J.L. Sessler, H. Maeda, T. Mizuno, V.M. Lynch, H. Furuta, Chem. Commun. 8 (2002) 862-863.
[37] M.M. Heravi, B. Baghernejad, H.A. Oskooie, Tetrahedron Lett. 50 (2009) 767-769.
[38] R. Mirsafaei, M.M. Heravi, S. Ahmadi, M.H. Moslemin, T. Hosseinnejad, J. Mol. Catal. A: Chem. 402 (2015) 100-108.
[39] E. Hashemi, Y.S. Beheshtiha, S. Ahmadi, M.M. Heravi, Trans. Met. Chem. 39 (2014) 593-601.
[40] B. Zhao, Y. Wang, H. Guo, J. Wang, Y. He, Z. Jiao, M. Wu, Mater. Sci. Poland 25 (2007) 1143-1148.
[41] M. Monier, D.M. Ayad, Y. Wei, A.A. Sarhan, React. Funct. Polym. 70 (2010) 257-266.
[42] A. Ayati, B. Tanhaei, F.F. Bamoharram, A. Ahmadpour, P. Maydannik, M. Sillanpää, Sep. Pur. Technol. 171 (2016) 62-68.
[43] F.F. Bamoharram, Molecules 14 (2009) 3124-3221.
[44] B. Tanhaei, A. Ayati, M. Lahtinen, B.M. Vaziri, M. Sillanpää, J. Appl. Polym. Sci. 133 (2016) 43466.
[45] B. Tanhaei, A. Ayati, F.F. Bamoharram, M. Lahtinen, M. Sillanpää, J. Chem. Technol. Biotechnol. 91 (2016) 1452-1460.
[46] E.L. Mogilevskaya, T.A. Akopova, A.N. Zelenetskii, A.N. Ozerin, Polym. Sci. Series A 48 (2006) 116-123.
