Abstract
A simple and practical procedure for synthesis of 2-arylbenzimidazoles by a one-pot condensation of o-phenylenediamine with aromatic aldehydes in the presence of a catalytic amount of M(NO3)2·6H2O (M = Mn, Fe, Co, Ni, Cu) in ethanol at room temperature is described. Major advantages of this practical procedure are use of a readily available catalyst, high yields, short reaction times, and simplicity of the reaction and workup.
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G.L. Gravatt, B.C. Baguley, W.R. Denny, J. Med. Chem. 37, 4338 (1994)
S.M. Abu-Bakr, F.A. Bassyouni, M.A. Rehim, Res. Chem. Intermed. (2012). doi: 10.1007/s11164-012-0569-y
J.S. Kim, B. Gatto, C. Yu, A. Liu, L.F. Liu, V. La, J. Med. Chem. 39, 992 (1996)
D.A. Horton, G.T. Bourne, M.L. Smythe, Chem. Rev. 103, 893 (2003)
A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach, B.L. Townsend, J. Med. Chem. 41, 1252 (1998)
A. Mobinikhaledi, N. Foroughifar, M. Kalhor, M. Mirabolfathy, J. Heterocycl. Chem. 47, 77 (2010)
J.S. Mason, I. Morize, P.R. Menard, D.L. Cheney, C. Hume, R.F. Labaudiniere, J. Med. Chem. 42, 3251 (1999)
R. Iemura, T. Kawashima, T. Fukuda, K. Ito, G.J. Tsukamoto, J. Heterocycl. Chem. 24, 31 (2009)
Y. Bai, J. Lu, Z. Shi, B. Yang, Synlett. 544 (2001)
E. Hasegawa, A. Yoneoka, K. Suzuki, T. Kato, T. Kitazume, K. Yangi, Tetrahedron 55, 12957 (2001)
P. Salehi, M. Dabiri, M.A. Zolfigol, S. Otokesh, M. Baghbanzadeh, Tetrahedron Lett. 47, 2557 (2006)
R.R. Nagawade, D.B. Shinde, Chin. Chem. Lett. 17, 453 (2006)
G.R. Jadhav, M.U. Shaikh, R.P. Kale, C.H. Gill, Chin. Chem. Lett. 20, 292 (2009)
M. Shen, C.J. Cai, Fluorine Chem. 128, 232 (2007)
A. Mobinikhaledi, N. Foroughifar, M. Zendehdel, M. Jabbarpour, Syn. React. Inorg. Met-org. Chem. 38, 390 (2008)
X. Han, H. Ma, Y. Wang, Russ. J. Org. Chem. 863 (2008)
K.H. Bûchel, Z. Naturforsch. 25B, 934 (1970)
A. Mobinikhaledi, A. Khajeh-Amiri, Res. Chem. Intermed. (2012). doi 10.1007/s11164-012-0707-6
A. Mobinikhaledi, M. Zendehdel, J.F. Hasanvand, Syn. React. Inorg. Met-org. Chem. 37, 175 (2007)
A. Mobinikhaledi, N. Foroughifar, M.A. Amrollahi, Asian J. Chem. 17, 1301 (2005)
M. Zendehdel, A. Mobinikhaledi, J.F. Hasanvand, J. Incl. Phenom. Macro 59, 41 (2007)
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Kalhor, M., Mobinikhaledi, A. & Jamshidi, J. Synthesis of 2-arylbenzimidazoles catalyzed by transition metal nitrates. Res Chem Intermed 39, 3127–3133 (2013). https://doi.org/10.1007/s11164-012-0825-1
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DOI: https://doi.org/10.1007/s11164-012-0825-1