Solvent-free synthesis and characterization of antibacterial azo dyes in the presence of Bronsted-acid ionic liquid as a green catalyst

Authors

1 Departement of Organic Chemistry, Faculty of Chemistry, University of Kashan, Kashan, I.R. Iran.

2 School of Chemistry, Damghan University, Damghan, I.R. Iran.

Abstract

A convenient and efficient direct protocol for the preparation of antibacterial azo dyes by the reaction of 2-naphthol with aromatic amines in the presence of catalytic amount of N-methyl-2-pyrrolidonium hydrogen sulfate ([H-NMP]HSO4) was carried out under solvent free conditions. This method has some advantages such as: easy work-up and easy separation of catalyst from the reaction mixture. The in vitro antibacterial activities of some compounds were studied using gram positive and negative microorganisms.

Keywords


[1] H.A. Dabbagh, A. Teimouri, A. R. Najafi Chermahini, Dyes Pigments, 73 (2007) 239-244.
[2] T. Robinson, G. McMullan, R. Marchant, P. Nigam, Bioresource Technol., 77 (2001) 247-255.
[3] G. Viscardi, P. Quagliotto, C. Barolo, G. Caputo, G. Digilio, I. Degani, E. Barni, Dyes Pigments, 57 (2003) 87-95.
[4] A. Fraleoni-Morgera, C. Della-Casa, P. Costa-Bizzarri, M. Lanzi, A. Missiroli, Macromolecule, 38 (2005) 3170-3175.
[5] H. Zolinger, Diazo and Azo Chemistry, Interscience publishers Inc. New York, 1961.
[6] A. Zarei, A.R. Hajipour, L. Khazdooz, B.F. Mirjalili, R.A. Najafi, Dyes Pigments, 81 (2009) 240-244.
[7] A. Morsy, M. El-Apasery, J. Appl. Poly. Sci., 109 (2008) 695-699.
[8] N. Noroozi-Pesyan, J. Khalafy, Z. Malekpoor, Prog. Color Colorants Coat., 1 (2009) 61-70.
[9] N. Noroozi-Pesyan, J. Khalafy, Z. Malekpoor, J. Chinese Chem. Soc. Taip., 56 (2009) 1018-1027.
[10] Y. Moglie. C. Vitale, G. Radivoy, Tetrahedron Lett., 49 (2008) 1828-1831.
[11] F. Ahmed Khan, J. Dash, C. Sudheer, R.K. Gupta, Tetrahedron Lett., 44 (2003) 7783-7787.
[12] A. Lycka, A. Kolonicny, P. Simunek, V. Machacek, Dyes Pigments, 72 (2007) 208-211.
[13] H. Valizadeh, A. Shomali, Dyes Pigments, 92 (2012) 1138-1143.
[14] D.L. Astolfi, F.C. Mayville, Tetrahedron Lett., 44 (2003) 9223-9224.
[15] K.N. Gaind, J.M. Khanna, Indian J. Pharm., 26 (1964) 34-38.
[16] M.P. Piste, D.P. Indalkar, D.N. Zambare, P.S. Mundada, Int. J. Chem. Res., 3 (2012) 25-29.
[17] L.S. Goodman, A. Gilman, The Pharmacological Basis of Therapeutics, McMillian, New York, 1970.
[18] W. Modell, Science, 89 (1939) 349-350.
[19] W.H. Ojala, C.R. Ojala, W.B. Gleason, Antiviral Chem. Chemotherapy, 6 (1995) 25-33.
[20] G.L. Kenyon, K.A. Johnson, J. Biol. Chem., 37 (2004) 38424-38432.
[21] L.R. Al-rubaie, R.L. Mhessn, E-J. Chem., 9 (2012) 465-470.
[22] G. Swati, R. Karnawat. I.K. Sharma, P.S. Verma, Int. J. Appl. Biol. Pharm. Techol., 2 (2011) 332-338.
[23] A. Chakraborty, P.K. Saha, C. Datta, 7th International Conference, TEXSCI, Liberec, Czech Republic, 2010.
[24] B.B.F. Mirjalili, A. Bamoniri, A. Akbari, Iran. J. Catal., 1 (2011) 87-92.
[25] A. Bamoniri, B.B.F. Mirjalili, A.Ghorbani-Choghamarani, M. E. Yazdanshenas, A. Shayanfar, A. Akbari, Iran. J. Catal., 1 (2011) 51-54.
[26] A. Bamoniri, B.B.F. Mirjalili, S. Nazemian, Iran. J. Catal., 2 (2012) 17-21.
[27] A. Bamoniri, B.B.F. Mirjalili, A.A. Jafari, F. Abasaltian, Iran. J. Catal., 2 (2012) 73-76.
[28] A. R. Hajipour, A. Rajaei, A.E. Ruoho, Tetrahedron Lett., 50 (2009) 708-7011.
[29] Colour Index, Society of Dyers and Colourists, Bradford, U.K. 1971.
[30] H.A. Tang, L.F. Wang, R.D. Yang, Transition Metal Chemistry, 28 (2003) 395-398.