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Synthesis and Structural Characterization of 2-(Hydroxyethoxy Substituted)phenyl Benzimidazoles
Corresponding Author(s) : Hai-Bin Gu
Asian Journal of Chemistry,
Vol. 27 No. 5 (2015): Vol 27 Issue 5
Abstract
In this paper, using o-phenylendiamine, hydroxyl substituted benzaldehyde and chlorohydrin as starting materials, four 2-(hydroxyethoxy substituted)phenyl benzimidazoles were synthesized by two different routes. In route I, the hydroxyl substituted benzaldehyde firstly reacted with o-phenylendiamine to get the intermediates 2-(hydroxyl substituted)phenyl benzimidazoles which then were used to synthesize the final products by the o-hydroxyethylation reaction with chlorohydrin. In route II, the hydroxyethoxy substituted benzaldehyde was firstly synthesized through the o-hydroxyethylation reaction and then reacted with o-phenylendiamine. Results show that route I is suitable only for the target compounds in which hydroxyethoxy group is located in para- and meta-position of benzimidazole in the benzene ring. For the synthesis of 2-(o-hydroxyethoxy)phenyl benzimidazole, route II is the only choice because of its strong steric hindrance. The structures of the four new compounds were characterized and confirmed by elemental analysis, IR, 1H NMR, 13C NMR and single-crystal X-ray diffraction analysis.
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References
Y. Wang, Q.F. Zhou, G.W. Lin, L.L. Di and T. Lu, Chin. J. Struct. Chem., 30, 97 (2011).
L. Gou, H.X. Zhang, X.Y. Fan, D.L. Li and L. Li, Chin. J. Struct. Chem., 29, 1394 (2010).
C.G. Sun, M.H. Zeng, K.Z. Xu and J.R. Song, Chin. J. Struct. Chem., 31, 1662 (2012).
D.F. Qiu, Y.L. Li, H.W. Wang and Y.C. Guo, Chin. J. Struct. Chem., 29, 811 (2010).
J. Hu, P. Wang, J.K. Wang and Y.H. Xu, Chin. J. Struct. Chem., 31, 1745 (2012).
S.G. Liu, Z.L. Chen, K. Liang and X.L. Chen, Chin. J. Struct. Chem., 32, 637 (2013).
F.F. Jian, F.L. Bei, X. Wang and L.D. Lu, Chin. J. Struct. Chem., 22, 382 (2003).
Y.C. Guo, L.H. Zhuo, Y.Y. Zhao, X.Z. Yao and Q.Z. Huang, Chin. J. Struct. Chem., 27, 1333 (2008).
M.H. Kim, J.S. Ryu and J.M. Hah, Bioorg. Med. Chem. Lett., 23, 1639 (2013); doi:10.1016/j.bmcl.2013.01.082.
X.X. Ren, J.Y. Chen and X.Y. Le, Chin. J. Chem., 29, 1380 (2011); doi:10.1002/cjoc.201180257.
P. Vicini, M. Incerti, L. Amoretti, V. Ballabeni, M. Tognolini and E. Barocelli, Farmaco, 57, 363 (2002); doi:10.1016/S0014-827X(02)01219-3.
Y.B. Bai, A.L. Zhang, J.J. Tang and J.-M. Gao, J. Agric. Food Chem., 61, 2789 (2013); doi:10.1021/jf3053934.
S.H. Nile, B. Kumar and S.W. Park, Chem. Biol. Drug Des., 82, 290 (2013); doi:10.1111/cbdd.12141.
E. Mentese, N. Karaali, F.Yilmaz, S. Ülker and B. Kahveci, Arch. Pharmazie, 346, 556 (2013); doi:10.1002/ardp.201300050.
T. Nagai, Y. Fukushima, T. Kuroda, H. Shimizu, S. Sekiguchi and K. Matsui, Bull. Chem. Soc. Jpn., 46, 2600 (1973); doi:10.1246/bcsj.46.2600.
M.A. Chari, D. Shobha, E.R. Kenawy, S.S. Al-Deyab, B.V.S. Reddy and A. Vinu, Tetrahedron Lett., 51, 5195 (2010); doi:10.1016/j.tetlet.2010.07.132.
N.V. Gabriel, M.D. Hermenegilda, A.C. Francisco, L.R. Ismael, V.M. Rafael, M.M. Omar and E.S. Samuel, Bioorg. Med. Chem. Lett., 16, 4169 (2006); doi:10.1016/j.bmcl.2006.05.082.