Melamine trisulfonic acid catalyzed regioselective nitration of aromatic compounds under solvent-free conditions

Authors

1 Young Research Club, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran

2 Department of Chemistry, College of Science, University of Guilan, Rasht, Iran

3 Department of chemistry, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran

Abstract

A simple, mild and efficient method for the regioselective nitration of various aromatic compounds using
poly(4-vinylpyridinium nitrate) (P4VPyN) in the presence of melamine trisulfonic acid (MTSA), is reported.
This method provides several advantages such as good selectiveity between ortho and para positions of
aromatic compounds, clean procedure, simple work-up, short reaction times, solvent-free conditions and
high yields of products. This methodology is useful for nitration of activated and deactivated aromatic rings.

Keywords


[1] G.A. Olah, R. Malhotra, S,C. Narang, Nitration: Methods and Mechanism, VCH, New York,1989.
[2] A.M. Tasneem, K.C. Rajanna, P.K. Saiprakash, Synth.Commun. 31 (2001) 1123-1127.
J. Albadi et al., J. Iranian Chem. Res. 5 (3) (2012) 155-159
159
[3] P. Manjo, S. Shriniwas, Synth.Commun. 40 (2010) 3734 -3738.
[4] A.R. Hajipour, A.E. Ruoho, Tetrahedron Lett 46 (2005) 8307-8310.
[5] S.M. Kemdeo, V.S. Sapkal, G.N. Chaudhari, J. Mol. Catal A: Chem. 323 (2010) 70-77.
[6] P.C. Wang, M. Lu, Tetrahedron Lett 52 (2011) 1452-1455.
[7] W.P.Yin, M. Shi, Tetrahedron. 61 (2005) 1086-1087.
[8] D. Koley, O.C. Colon, S.N. Savinov, Org. Lett. 11 (2009) 4172-4175.
[9] G. Cheng, X. Duan, X. Qi, C. Lu, Catal. Commun. 10 (2008) 201-204
[10] N. Nowrouzi, M.Z. Jonaghani, Tetrahedron Lett 52 (2011) 5081-5082.
[11] H. Goudarziafshar, Chin. Chem. Lett. 23 (2012) 458-461.
[12] F. Shirini, M.A. Zolfigol, J. Albadi, Synth. Commun 40 (2010) 910-914
[13] F. Shirini, M.A. Zolfigol, J. Albadi, Chin. Chem. Lett. 22 (2011) 318-321.
[14] F. Shirini, M.A. Zolfigol, J. Albadi, Bull. Korean. Chem. Soc. 31 (2010) 1119-1120.
[15] F. Shirini, M.A. Zolfigol, J. Albadi, J. Iran. Chem, Soc. 7 (2010) 895-899.
[16] F. Shirini, M.A. Zolfigol, A.R. Aliakbar, J. Albadi, Synth. Commun 40 (2010) 1022-1028
[17] A. Ghorbani-Choghmani, S. Sardari, Chin. J. Chem. 31 (2010) 1347-1350.
[18] H. Tajik, M.A. Zolfigol, J. Albadi, R. Eslami, Synth. Commun. 37(2007) 2771-2776.