Document Type: Original Article

Authors

1 ‎Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran

2 Department of Chemistry, Ahvaz Branch, Islamic Azad University, Ahvaz, Iran

10.33945/SAMI/CHEMM/2020.3.9

Abstract

Tri substituted imidazole derivatives were synthesized with the combinations of phenanthroquinone, benzealdehyde derivatives at the presence of ammonium acetate that catalyzed by Lewis acid. In all reactions, polar solvent was used and the reactions were carried out under the reflux conditions. The structure of all compounds was confirmed using the IR and 1HNMR. This method revealed several advantages including, excellent yields, simplicity of operation and easy separation. The results showed that, products formed in high yields and low reaction times. Also, the metal atom of Lewis acid catalyst increased the reactivity of substrate and the reaction time.

Graphical Abstract

Keywords

[1] D’Souza D.M., Mueller T.J.J. Chem. Soc. Rev., 2007, 36:1095

[2] Domling A. Chem. Rev., 2006, 17:106

[3] Khan A.J., Basheer M. Orient. J. Chem., 2011, 27:1759

[4] (a) Setamdideh D., Karimi Z., Rahimi F. Orient. J. Chem., 2011, 27:1621 (b) Samimi H.A., Vaezzadeh H., Chem. Methodol., 2018, 2:260

[5] Tempest P.A. Curr. Opin. Drug. Discov. Devel., 2005, 8:776

[6] Welsch S.J., Umkehrer M., Kalinski C., Ross G., Burdack C., Kolb J., Wild M., Ehrlich A., Wessjohann L.A. Tetrahedron Lett., 2015, 56:1025

[7] Gupta V., Kant V. Sci. Int., 2013, 1:253

[8] Gupta P., Gupta J.K., Int. J. Modern Chem, 2015, 7:60

[9] Joule J.A., Mills K. Heterocyclic Chemistry. 5 th ed., John Wiley & Sons: Chichester; 2010, p 455

[10] Zhang L., Peng X.M., Damu G.L.V., Geng R.X., Zhou C.H. Med. Res. Rev., 2014, 34:340

[11] Wittine K., Stipkovic Babic M., Makuc D., Plavec J., Kraljevic S., Sedic M., Paveli K., Leyssen Neyts P.J., Balzarini Mintas J.M. Bioorg. Med. Chem., 2012, 20:3675

[12] Rehman S., Ikram M., Rehman S., Faiz A. Bull. Chem. Soc. Ethiop., 2010, 24:201

[13] Mohammadi M.K., Firuzi O., Khoshneviszadeh M., Razzaghi-Asl N., Sepehri S., Miri R. DARU J. Pharmaceutical Sci., 2014, 22:2

[14] Shelke K.F., Suryakant B., Gopal K., Bapurao B., Murlidhar S. Green Chem. Lett. Rev., 2010, 3:27

[15] (a) Maleki B., Keshvari H., Mohammadi A. Oriental. J. Chem., 2012, 28:1207 (b) Soleiman-Beigi M., Arzehgar Z., Monatsh. Chem., 2016, 147: 1759

[16] Gadekar L.S., Mane S.R., Katkar S.S., Arbad B.R., Lande M.K. Cent. Eur. J. Chem., 2009, 7:550

[17] Sajjadifar S., Arzehgar Z., Ghayuri A. J. Chin. Chem. Soc., 2018, 65:205

[18] Mohammadi R., Sajjadi A. J. Med. Chem. Sci., 2019, 2:55

[19] Gupta S., Lakshman M. J. Med. Chem. Sci., 2018, 2:51

[20] Liang C., Huajian Z., Wang J., Hong L. Molecules, 2019, 24:893

[21] Miri R., Firuzi O., Peymani P., Zamani M., Mehdipour A.R., Heydari Z.,Masteri Farahani M., Shafiee A. Chem. Biol. Drug. Des., 2012, 79:68

[22] Azizian J., Mohammadi M.K., Firuzi O., Mirza B., Miri R. Chem. Biol. Drug. Des., 2010, 75:375

[23] Azizian J., Mohammadi M.K., Firuzi O., Razzaghi-Asl N., Miri R. Med. Chem. Res., 2012, 21:3730