Melamine trisulfonic acid catalyzed regioselective nitration of aromatic compounds under solvent-free conditions
Subject Areas : Journal of the Iranian Chemical ResearchJalal Albadi 1 , Farhad Shirinib 2 , Masoumeh Abedini 3 , Tayebeh Seiadatnasab 4
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, College of Science, University of Guilan, Rasht, Iran
4 - Department of chemistry, Gachsaran Branch, Islamic Azad University, Gachsaran, Iran
Keywords: Nitration, Melamine trisulfonic acid, Aromatic compounds,
Abstract :
A simple, mild and efficient method for the regioselective nitration of various aromatic compounds usingpoly(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 ofaromatic compounds, clean procedure, simple work-up, short reaction times, solvent-free conditions andhigh yields of products. This methodology is useful for nitration of activated and deactivated aromatic rings.
[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.