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Synthesis of 2-Aryl-1-arylmethyl-1H-benzimidazoles Catalyzed by Brønsted Acidic Ionic Liquid under Ultrasonic Irradiation
Corresponding Author(s) : Chun Wang
Asian Journal of Chemistry,
Vol. 26 No. 7 (2014): Vol 26 Issue 7
Abstract
A series of 2-aryl-1-arylmethyl-1H-benzimidazoles were synthesized through the condensation reactions of aromatic aldehydes and o-phenylenediamine using Brønsted acidic ionic liquid, 3-methyl-1-(3-sulfopropyl)-imidazolium trifluoro acetate, as catalyst under ultrasonic irradiation condition. The yields of the products were in the range from 85 % to 97 %. The Brønsted acidic ionic liquid can be recovered and reused at least five consecutive cycles without significant loss of its catalytic activity. The results indicated that the proposed method is easy, efficient and environmental friendly for the preparation of 2-aryl-1-arylmethyl-1H-benzimidazoles.
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References
H. Zarrinmayeh, A.M. Nunes, P.L. Ornstein, D.M. Zimmerman, M.B. Arnold, D.A. Schober, S.L. Gackenheimer, R.F. Bruns, P.A. Hipskind, T.C. Britton, B.E. Cantrell and D.R. Gehlert, J. Med. Chem., 41, 2709 (1998); doi:10.1021/jm9706630.
J. Zhao, D. Arnaiz, B. Griedel, B. Sakata, J. Dallas, M. Whitlow, L. Trinh, J. Post, A. Liang, M. Morrissey and K. Shaw, Bioorg. Med. Chem. Lett., 10, 963 (2000); doi:10.1016/S0960-894X(00)00139-6.
H.M. Elokdah, S.Y. Chai and T.S. Sulkowski, Chem. Abstr., 129, 58784g (1998).
E. Lukevics, P. Arsenyan, I. Shestakova, I. Domracheva, A. Nesterova and O. Pudova, Eur. J. Med. Chem., 36, 507 (2001); doi:10.1016/S0223-5234(01)01241-7.
A.A. Spasov, I.N. Yozhitsa, L.I. Bugaeva and V.A. Anisimova, Pharm. Chem. J., 33, 232 (1999); doi:10.1007/BF02510042.
A.R. Porcari, R.V. Devivar, L.S. Kucera, J.C. Drach and L.B. Townsend, J. Med. Chem., 41, 1252 (1998); doi:10.1021/jm970559i.
I. Tamm, Science, 120, 847 (1954); doi:10.1126/science.120.3125.847.
(a) Y. Bai, J. Lu, Z. Shi and B. Yang, Synlett, 544 (2001); (b) E. Hasegawa, A. Yoneoka, K. Suzuki, T. Kato, T. Kitazume and K. Yanagi, Tetrahedron, 55, 12957 (1999); doi:10.1016/S0040-4020(99)00804-2.
R. Trivedi, S.K. De and R.A. Gibbs, J. Mol. Catal. Chem., 245, 8 (2006); doi:10.1016/j.molcata.2005.09.025.
P.N. Preston, eds.: A. Weissberger and E.C. Taylor; In: Chemistry of Heterocyclic Compounds, Wiley, New York, Part 1, vol. 40, p. 6 (1981).
M.R. Grimmett, eds.: A.R. Katritzky and C.W. Rees, Comprehensive Heterocyclic Chemistry, Pergamon, Oxford, vol. 5, p. 457 (1984).
K. Bahrami, M.M. Khodaei and F. Naali, J. Org. Chem., 73, 6835 (2008); doi:10.1021/jo8010232.
R. Fazaeli and H. Aliyan, Appl. Catal. A, 353, 74 (2009); doi:10.1016/j.apcata.2008.10.035.
K. Bahrami, M.M. Khodaei and F. Naali, Synlett, 569 (2009); doi:10.1055/s-0028-1087911.
S. Rostamizadeh, A.M. Amani, R. Aryan, H.R. Ghaieni and L. Norouzi, Monatsh. Chem., 140, 547 (2009); doi:10.1007/s00706-008-0087-1.
S. Narayan, J. Muldoon, M.G. Finn, V.V. Fokin, H.C. Kolb and K.B. Sharpless, Angew. Chem. Int. Ed., 44, 3275 (2005); doi:10.1002/anie.200462883.
V. Ravi, E. Ramu, K. Vijay and A. Srinivas Rao, Chem. Pharm. Bull. (Tokyo), 55, 1254 (2007); doi:10.1248/cpb.55.1254.
P. Salehi, M. Dabiri, M.A. Zolfigol, S. Otokesh and M. Baghbanzadeh, Tetrahedron Lett., 47, 2557 (2006); doi:10.1016/j.tetlet.2006.02.049.
S.S. Pawar, D.V. Dekhane, M.S. Shingare and S.N. Thore, Chin. Chem. Lett., 19, 1055 (2008); doi:10.1016/j.cclet.2008.06.028.
L.M. Dudd, E. Venardou, E. Garcia-Verdugo, P. Licence, A.J. Blake, C. Wilson and M. Poliakoff, Green Chem., 5, 187 (2003); doi:10.1039/b212394k.
J. Fraga-Dubreuil, K. Bourahla, M. Rahmouni, J.P. Bazureau and J. Hamelin, Catal. Commun., 3, 185 (2002); doi:10.1016/S1566-7367(02)00087-0.
A. Arfan and J.P. Bazureau, Org. Process Res. Dev., 9, 743 (2005); doi:10.1021/op058002x.
J.-Z. Gui, X.-H. Cong, D. Liu, X.-T. Zhang, Z.-D. Hu and Z.-L. Sun, Catal. Commun., 5, 473 (2004); doi:10.1016/j.catcom.2004.06.004.
(a) T. Welton, Chem. Rev., 99, 2071 (1999); doi:10.1021/cr980032t.; (b) J. Dupont, R.F. De Souza and P.A.Z. Suarez, Chem. Rev., 102, 3667 (2002); doi:10.1021/cr010338r.; (c) N. Jain, A. Kumar, S. Chauhan and S.M.S. Chauhan, Tetrahedron, 61, 1015 (2005); doi:10.1016/j.tet.2004.10.070.; (d) S. Chowdhury, R.S. Mohan and J.L. Scott, Tetrahedron, 63, 2363 (2007); doi:10.1016/j.tet.2006.11.001.
(a) W.-H. Liu, S.-T. Gao, C. Feng, X.-H. Zang, X. Zhou, J.-J. Ma and C. Wang, Chin. J. Org. Chem., 32, 962 (2012); doi:10.6023/cjoc1109181.; (b) J.-J. Ma, X. Zhou, X.-H. Zang, C. Wang, Z. Wang, J.-C. Li and Q. Li, Aust. J. Chem., 60, 146 (2007); doi:10.1071/CH06225.; (c) J.-J. Ma, S.-T. Gao, Z. Li, R.-X. Tang, H.-Y. Liu, C. Wang and Y. Gao, Chin. J. Org. Chem., 28, 339 (2008); (d) J.-J. Ma, X.-H. Zang, X. Zhou, C. Wang, J.-C. Li and Q. Li, Indian J. Chem., 46B, 2045 (2007); (e) C. Wang, J.-J. Ma, X. Zhou, X.-H. Zang, Z. Wang, Y.-J. Gao and P.-L. Cui, Synth. Commun., 35, 2759 (2005); doi:10.1080/00397910500288254.
S. Tang, A.M. Scurto and B. Subramaniam, J. Catal., 268, 243 (2009); doi:10.1016/j.jcat.2009.09.022.
S. Perumal, S. Mariappan and S. Selvaraj, ARKIVOC, 46 (2004).