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Nano ZnO Catalyzed One-Pot Synthesis of Benzimidazoles from o-Phenylenediamine with Aldehydes
Corresponding Author(s) : Dong Mei Cui
Asian Journal of Chemistry,
Vol. 27 No. 11 (2015): Vol 27 Issue 11
Abstract
Nano-ZnO was found to be a highly efficient and reusable heterogeneous catalyst for the one-pot synthesis of substituted benzimidazoles from aromatic aldehydes with o-phenylenediamine in moderate to good yield. The spent catalyst can be easily recovered and reused for five cycles with consistent activity.
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- Y. Bai, J. Lu, Z. Shi and B. Yang, Synlett, 544 (2001); doi:10.1055/s-2001-12339.
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- E.D. Friedman and E.G. Platzer, Biochim. Biophys. Acta, 630, 271 (1980); doi:10.1016/0304-4165(80)90431-6.
- 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.
- L.-H. Du and Y.-G. Wang, Synthesis, 675 (2007).
- K. Bahrami, M.M. Khodaei and F. Naali, J. Org. Chem., 73, 6835 (2008); doi:10.1021/jo8010232.
- K. Bahrami, M.M. Khodaei and I. Kavianinia, Synthesis, 547 (2007); doi:10.1055/s-2007-965878.
- S. Lin and S.L. Yang, Tetrahedron Lett., 46, 4315 (2005); doi:10.1016/j.tetlet.2005.04.101.
- M. Adharvana Chari, D. Shobha and T. Sasaki, Tetrahedron Lett., 52, 5575 (2011); doi:10.1016/j.tetlet.2011.08.047.
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- P.P. Ghosh and A.R. Das, Tetrahedron Lett., 53, 3140 (2012); doi:10.1016/j.tetlet.2012.04.033.
- U.U. Indulkar, S.R. Kale, M.B. Gawande and R.V. Jayaram, Tetrahedron Lett., 53, 3857 (2012); doi:10.1016/j.tetlet.2012.05.048.
- G.R. Jadhav, M.U. Shaikh, R.P. Kale and C.H. Gill, Chin. Chem. Lett., 20, 535 (2009); doi:10.1016/j.cclet.2008.12.004.
- K. Khosravi and S. Kazemi, Chin. Chem. Lett., 23, 61 (2012); doi:10.1016/j.cclet.2011.09.028.
- R. Chebolu, D.N. Kommi, D. Kumar, N. Bollineni and A.K. Chakraborti, J. Org. Chem., 77, 10158 (2012); doi:10.1021/jo301793z.
- N. Iravani, N.S. Mohammadzade and K. Niknam, Chin. Chem. Lett., 22, 1151 (2011); doi:10.1016/j.cclet.2011.04.012.
- C.S. Cho and J.U. Kim, Bull. Korean Chem. Soc., 29, 1097 (2008); doi:10.5012/bkcs.2008.29.6.1097.
- L.S. Gadekar, B.R. Arbad and M.K. Lande, Chin. Chem. Lett., 21, 1053 (2010); doi:10.1016/j.cclet.2010.03.038.
- M. Chakrabarty, R. Mukherjee, S. Karmakar and Y. Harigaya, Monatsh. Chem., 138, 1279 (2007); doi:10.1007/s00706-007-0714-2.
- B. Das, B.S. Kanth, K.R. Reddy and A.S. Kumar, J. Heterocycl. Chem., 45, 1499 (2008); doi:10.1002/jhet.5570450542.
- I. Sheikhshoaie, F. Belaj and W.M.F. Fabian, J. Mol. Struct., 794, 244 (2006); doi:10.1016/j.molstruc.2006.02.022.
- J.-P. Wan, S.-F. Gan, J.-M. Wu and Y. Pan, Green Chem., 11, 1633 (2009); doi:10.1039/b914286j.
- B.H. Kim, R. Han, T.H. Han, Y.M. Jun, W. Baik and B.M. Lee, Heterocycles, 57, 5 (2002); doi:10.3987/COM-01-9381.
- R.R. Nagawade and D.B. Shinde, Russ. J. Org. Chem., 42, 453 (2006); doi:10.1134/S1070428006030201.
- N.V. Subba Rao and C.V. Ratnam, Proc. Indian Acad. Sci., 47, 81 (1958).
- G. Navarrete-Vázquez, S. Hidalgo-Figueroa, M. Torres-Piedra, J. Vergara-Galicia, J.C. Rivera-Leyva, S. Estrada-Soto, I. León-Rivera, B. Aguilar-Guardarrama, Y. Rios-Gómez and R. Villalobos-Molina, Bioorg. Med. Chem., 18, 3985 (2010); doi:10.1016/j.bmc.2010.04.027.
References
Y. Bai, J. Lu, Z. Shi and B. Yang, Synlett, 544 (2001); doi:10.1055/s-2001-12339.
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.
G.A. Molander and K. Ajayi, Org. Lett., 14, 4242 (2012); doi:10.1021/ol301956p.
G.L. Gravatt, B.C. Baguley, W.R. Wilson and W.A. Denny, J. Med. Chem., 37, 4338 (1994); doi:10.1021/jm00051a010.
J.S. Kim, B. Gatto, C. Yu, A. Liu, L.F. Liu and E.J. La Voie, J. Med. Chem., 39, 992 (1996); doi:10.1021/jm950412w.
T. Roth, M.L. Morningstar, P.L. Boyer, S.H. Hughes, R.W. Buckheit Jr. and C.J. Michejda, J. Med. Chem., 40, 4199 (1997); doi:10.1021/jm970096g.
D.A. Horton, G.T. Bourne and M.L. Smythe, Chem. Rev., 103, 893 (2003); doi:10.1021/cr020033s.
Y. Bansal and O. Silakari, Bioorg. Med. Chem., 20, 6208 (2012); doi:10.1016/j.bmc.2012.09.013.
E.D. Friedman and E.G. Platzer, Biochim. Biophys. Acta, 630, 271 (1980); doi:10.1016/0304-4165(80)90431-6.
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.
L.-H. Du and Y.-G. Wang, Synthesis, 675 (2007).
K. Bahrami, M.M. Khodaei and F. Naali, J. Org. Chem., 73, 6835 (2008); doi:10.1021/jo8010232.
K. Bahrami, M.M. Khodaei and I. Kavianinia, Synthesis, 547 (2007); doi:10.1055/s-2007-965878.
S. Lin and S.L. Yang, Tetrahedron Lett., 46, 4315 (2005); doi:10.1016/j.tetlet.2005.04.101.
M. Adharvana Chari, D. Shobha and T. Sasaki, Tetrahedron Lett., 52, 5575 (2011); doi:10.1016/j.tetlet.2011.08.047.
S.M. Inamdar, V.K. More and S.K. Mandal, Tetrahedron Lett., 54, 579 (2013); doi:10.1016/j.tetlet.2012.11.091.
M.L. Kantam, S. Priyadarshini, P.J. Amal Joseph, P. Srinivas, A. Vinu, K.J. Klabunde and Y. Nishina, Tetrahedron, 68, 5730 (2012); doi:10.1016/j.tet.2012.05.044.
P.P. Ghosh and A.R. Das, Tetrahedron Lett., 53, 3140 (2012); doi:10.1016/j.tetlet.2012.04.033.
U.U. Indulkar, S.R. Kale, M.B. Gawande and R.V. Jayaram, Tetrahedron Lett., 53, 3857 (2012); doi:10.1016/j.tetlet.2012.05.048.
G.R. Jadhav, M.U. Shaikh, R.P. Kale and C.H. Gill, Chin. Chem. Lett., 20, 535 (2009); doi:10.1016/j.cclet.2008.12.004.
K. Khosravi and S. Kazemi, Chin. Chem. Lett., 23, 61 (2012); doi:10.1016/j.cclet.2011.09.028.
R. Chebolu, D.N. Kommi, D. Kumar, N. Bollineni and A.K. Chakraborti, J. Org. Chem., 77, 10158 (2012); doi:10.1021/jo301793z.
N. Iravani, N.S. Mohammadzade and K. Niknam, Chin. Chem. Lett., 22, 1151 (2011); doi:10.1016/j.cclet.2011.04.012.
C.S. Cho and J.U. Kim, Bull. Korean Chem. Soc., 29, 1097 (2008); doi:10.5012/bkcs.2008.29.6.1097.
L.S. Gadekar, B.R. Arbad and M.K. Lande, Chin. Chem. Lett., 21, 1053 (2010); doi:10.1016/j.cclet.2010.03.038.
M. Chakrabarty, R. Mukherjee, S. Karmakar and Y. Harigaya, Monatsh. Chem., 138, 1279 (2007); doi:10.1007/s00706-007-0714-2.
B. Das, B.S. Kanth, K.R. Reddy and A.S. Kumar, J. Heterocycl. Chem., 45, 1499 (2008); doi:10.1002/jhet.5570450542.
I. Sheikhshoaie, F. Belaj and W.M.F. Fabian, J. Mol. Struct., 794, 244 (2006); doi:10.1016/j.molstruc.2006.02.022.
J.-P. Wan, S.-F. Gan, J.-M. Wu and Y. Pan, Green Chem., 11, 1633 (2009); doi:10.1039/b914286j.
B.H. Kim, R. Han, T.H. Han, Y.M. Jun, W. Baik and B.M. Lee, Heterocycles, 57, 5 (2002); doi:10.3987/COM-01-9381.
R.R. Nagawade and D.B. Shinde, Russ. J. Org. Chem., 42, 453 (2006); doi:10.1134/S1070428006030201.
N.V. Subba Rao and C.V. Ratnam, Proc. Indian Acad. Sci., 47, 81 (1958).
G. Navarrete-Vázquez, S. Hidalgo-Figueroa, M. Torres-Piedra, J. Vergara-Galicia, J.C. Rivera-Leyva, S. Estrada-Soto, I. León-Rivera, B. Aguilar-Guardarrama, Y. Rios-Gómez and R. Villalobos-Molina, Bioorg. Med. Chem., 18, 3985 (2010); doi:10.1016/j.bmc.2010.04.027.