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Synthesis and Characterization of 2,5-Disubstituted-1,3,4-oxadiazole Derivatives with Thioether Groups
Corresponding Author(s) : Zanariah Abdullah
Asian Journal of Chemistry,
Vol. 27 No. 7 (2015): Vol 27 Issue 7, 2015
Abstract
New 2,5-disubstituted-1,3,4-oxadiazole derivatives were synthesized by the reaction of 2-(ethylsulfanyl)benzohydrazide with CS2 in KOH to afford 5-[2-(ethylsulfanyl)phenyl]-1,3,4-oxadiazole-2(3H)-thione. On alkylation with benzylic halides in the presence of anhydrous potassium carbonate as a base and dry acetone as a solvent gave the new 1,3,4-oxadiazole derivatives. An attempt to design a series of new derivatives derived from thiosalicylic acid by coupling 1,3,4-oxadiazole with benzimidazole moiety and another 1,3,4-oxadiazole ring has been put forward for the first time. The structure of the compounds was confirmed by IR, 1H NMR,13C NMR and mass spectra.
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- P. Zeuthen, K.G. Knudsen and D. Whitehurst, Catal. Today, 65, 307 (2001); doi:10.1016/S0920-5861(00)00566-6.
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- C.-J. Chen, B.-A. Song, S. Yang, G.-F. Xu, P.S. Bhadury, L.-H. Jin, D.-Y. Hu, Q.-Z. Li, F. Liu, W. Xue, P. Lu and Z. Chen, Bioorg. Med. Chem., 15, 3981 (2007); doi:10.1016/j.bmc.2007.04.014.
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References
P. Zeuthen, K.G. Knudsen and D. Whitehurst, Catal. Today, 65, 307 (2001); doi:10.1016/S0920-5861(00)00566-6.
R.J. Wallace, Proc. Nutr. Soc., 63, 621 (2004); doi:10.1079/PNS2004393.
M. Mikołajczyk, S. Grzejszczak, A. Zatorski, B. Mlotkowska, H. Gross and B. Costisella, Tetrahedron, 34, 3081 (1978); doi:10.1016/0040-4020(78)87003-3.
M. Aydin, N. Arsu and Y. Yagci, Macromol. Rapid Commun., 24, 718 (2003); doi:10.1002/marc.200300019.
J. Halaschek-Wiener, Y. Kloog, V. Wacheck and B. Jansen, J. Invest. Dermatol., 120, 1 (2003); doi:10.1046/j.1523-1747.2003.12009.x.
A. Zarghi, S.A. Tabatabai, M. Faizi, A. Ahadian, P. Navabi, V. Zanganeh and A. Shafiee, Bioorg. Med. Chem. Lett., 15, 1863 (2005); doi:10.1016/j.bmcl.2005.02.014.
K.J. Shin, K.D. Koo, K.H. Yoo, Y.K. Kang, S.W. Park and D.J. Kim, Bioorg. Med. Chem. Lett., 11, 2397 (2001); doi:10.1016/S0960-894X(01)00451-6.
K. Fukuzumi, N. Ikeda and M. Egawa, J. Am. Oil Chem. Soc., 53, 623 (1976); doi:10.1007/BF02586274.
C.-J. Chen, B.-A. Song, S. Yang, G.-F. Xu, P.S. Bhadury, L.-H. Jin, D.-Y. Hu, Q.-Z. Li, F. Liu, W. Xue, P. Lu and Z. Chen, Bioorg. Med. Chem., 15, 3981 (2007); doi:10.1016/j.bmc.2007.04.014.
D. Kumar, S. Sundaree, E.O. Johnson and K. Shah, Bioorg. Med. Chem. Lett., 19, 4492 (2009); doi:10.1016/j.bmcl.2009.03.172.