Document Type: Original Research Article

Authors

Department of Chemistry, Payame Noor University, P.O. BOX 19395-4697 Tehran, Iran

10.33945/SAMI/ECC.2020.4.1

Abstract

CoFe2O4 is used as an efficient catalyst for reaction of benzoin, benzaldehydes, and ammonium acetate under mild and green conditions. This reaction is produced the corresponding 2,4,5-triarylimidazole lophine as the representative of multisubstituted imidazoles in high yields (99%), high purity (>98%) and short reaction time (10 min) in comparison to the previously reported approaches. The catalyst was separated easily by an external magnet. In addition, the recycled catalyst was reused several times without significant loss of catalytic properties.

Graphical Abstract

Keywords

[1] M. Sadeghi, S. Yekta, Iran. Chem. Commun., 2016, 4, 21-41.

[2] J. Shi, Chem. Rev., 2013, 113, 2139-2181.

[3] A.U. Itodo, O.M. Itodo, E. Iornumbe, M.O. Fayomi, Prog. Chem. Biochem. Res., 2019, 01, 50-59.

[4] B.S. Mohan, D. Ramadevi, K. Basavaiah, Prog. Chem. Biochem. Res., 2019, 02, 64-67.

[5] K.K. Gangu, S. Maddila, S.N. Maddila, S.B. Jonnalagadda, Molecules., 2016, 21, 1281-1296.

[6] K.K. Gangu, S. Maddila, S.N. Maddila, S.B. Jonnalagadda, J. Alloys Comp., 2017, 690, 817–824.

[7] H. Saeidian, F. Moradnia, Iran. Chem. Commun., 2017, 5, 252-261.

[8] I.E. Wachs, K. Routray, ACS Catal., 2012, 2, 1235-1246.

[9] G. Aguila, D. Salinas, R. Jiménez, S. Guerrero, P. Araya, J. Chil. Chem. Soc., 2016, 61, 3233-3238.

[10] A.R. Moosavi-Zare, H. Goudarziafshar, Z. Jalilian, Prog. Chem. Biochem. Res., 2019, 02, 59-63.

[11] M. Aghazadeh, Prog. Chem. Biochem. Res., 2019, 02, 34-39.

[12] K.K. Alisher, T.S. Khamza, Y.S. Ikbol, Prog. Chem. Biochem. Res., 2019, 02, 1-5.

[13] K.S. Niralwad, B.B. Shingate, M.S. Shingare, J. Heterocycl. Chem., 2011, 48, 742-754.

[14] A. Zare, A. Hasaninejad, A. Khalafi-Nezhad, A.R. Moosavi-Zare, M.H. Beyzavi, F. Khedri, F. Asadi, N. Hayati, A. Asifi, J. Iran Chem. Soc., 20107, 461-469.

[15] D.W. Seo, Y.D. Lim, S.H. Lee, S.C. Ur, W.G. Kim, Bull. Korean Chem. Soc., 2011, 32, 2633-2636.

[16] H. Li, J. Liu, J. Zhu, H. Wang, J. Korean Chem. Soc., 2011, 55, 685-690.

[17] M. Amir, I. Ahsan, W. Akhtar, S.A. Khan, I. Ali, Indian J. Chem., 2011, 50B, 207-213.

[18] A. Husain, S. Drabu, N. Kumar, M.M. Alam, S. Bawa, J. Pharm. Bioallied. Sci., 2013, 5, 154-161.

[19] A.K. Jain, R.K. Agrawal, V. Ravichandran, S. Sisodiya, Asian Pac. J. Trop. Med., 2010, 7, 271-274.

[20] A.M. Vijesh, M. Arun, S. Telkar, S.K. Peethambar, S. Rai, N. Isloor, European J. Med. Chem., 2011, 46, 3531-3536.

[21] V. Padmavathi, C. Prema kumara, B.C. Venkatesh, A. Padmaja, European J. Med. Chem., 2011, 46, 5317-5326.

[22] R. Ramachandran, M. Rani, S. Senthan, S. Kabilan, European J. Med. Chem., 2011, 46, 1926-1934.

[23] M. Gorsd, G. Sathicq, G. Romanelli, L. Pizzio, M. Blanco, J. Mol. Catal. A: Chem., 2016, 420, 294-302.

[24] J.F. Zhou, G.X. Gong, H.Q. Zhu, F.X. Zhu, Chinese Chem. Lett., 2009, 20, 1198-1200.

[25] J.F. Zhou, G.X. Gong, X.J. Sun, Y.L. Zhu, Synth. Commun., 2010, 40, 1134-1141.

[26] S. Samai, G.C. Nandi, P. Singh, M.S. Singh, Tetrahedron, 2009, 65, 10155-10161.

[27] A. Khorramabadi-zad, M. Azadmanesh, S. Mohammadi, S. Afr. J. Chem., 2013, 66, 244-247.

[28] B.H. Rotstein, S. Zaretsky, V. Rai, A.K. Yudin, Chem. Rev., 2014, 114, 8323-8359.

[29] R.S. Joshi, P.G. Mandhane, M.U. Shaikh, R.P. Kale, C.H. Gill, Chinese Chem. Lett., 2010, 21, 429-432.

[30] N.H. Peng, X.M. Peng, D.G. Zheng, F. Yu, M. Rao, Heterocycl. Comm., 2011, 17, 223-226.

[31] N. Azizi, N. Dado, A.K. Amiri, Can. J. Chem., 2012, 90, 195-198.

[32] M. Ashrafi, A. Davoodnia, F. Tavakoli-Hoseini, Bull. Korean Chem. Soc., 2013, 34, 1508-1512.

[33] J. Safari, Z. Zarnegar, S. Naseh, Z. Akbari, Iranian J. Catal., 2014, 4, 125-132.

[34] B. Maleki, SS. Sedigh Ashrafi, J. Mex. Chem. Soc., 2014, 58, 76-81.

[35] A. Maleki, Z. Alirezvani, J. Chil. Chem. Soc., 2016, 61(3), 3116-3119.

[36] S.A. Siddiqui, U.C. Narkhede, S.S. Palimkar, T. Daniel, R.J. Loholi, K.V. Srinivasan, Tetrahedron200561, 3539-3546.

[37] M. Kidwai, P. Mothsra, V. Bansal, R.K. Somvanshi, A.S. Ethayathulla, S. Dey, T.P. Singh, J. Mol. Catal. A: Chem., 2007, 265, 177-182.

[38] T.S. Ahooie, N. Azizi, I. Yavari, M.M. Hashemi, J. Iran. Chem. Soc., 2018, 15, 855-862.

[39] M.V. Chary, N.C. Keerthysri, K.V. Srinivasu, Catal. Comm., 2008, 9, 2013-2017.

[40] H. Ramezanalizadeh, Iran. Chem. Commun., 2018, 6, 192-208.

[41] M. KarimKoshteh, M. Bagheri, J. Mex. Chem. Soc., 2017, 61, 28-34.

[42] N.H. Hong, A.T. Raghavender, O. Ciftja, M.H. Phan, K. Stojak, H. Srikanth, Y.H. Zhang, Appl. Phys. A., 2013, 112, 323-327.

[43] N. Sanpo, C.C. Berndt, C. Wen, J. Wang, Acta Biomater., 2013, 9, 5830-5837.

[44] M. Mahdavi, F. Namvar, M.B. Ahmad, R. Mohamad, Molecules, 2013, 18, 5954-5964.

[45] A.M. Awwad, N.M. Salem, J. Nanosci. Nanotechnol., 2012, 2, 208-213.

[46] Y. Zhang, Z. Yang, B.P. Zhu, W. Yu, S. Chen, X.F. Yang, F. Jin, J. Ou-Yang, Ceram. Int., 2014, 40, 3439-3443.

[47] S.P. Dubey, M. Lahtinen, M. Sillanpaa, Process Biochem., 2010, 45, 1065-1071.

[48] M.W. Mushtaq, F. Kanwal, A. Batool, T. Jamil, M. Zia-ul-Haq, B. Ijaz, Q. Huang, Z. Ullah, J. Mater. Sci., 2017, 52, 9282-9293.