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Synthesis, Characterization and Biological Evaluation of Some Novel Azo-Imine Compounds
Corresponding Author(s) : K. Sunitha
Asian Journal of Chemistry,
Vol. 34 No. 3 (2022): Vol 34 Issue 3, 2022
Abstract
The oxidative cyclization of thiosemicarbazone (III) synthesized from reaction between substituted aryl aldehydes (I) with thiosemicarbazide (II) was done using ferric chloride as oxidative agent to get 2-amino-5-phenyl-1,3,4-thiadiazole (IV). 2-Amino-5-phenyl-1,3,4-thiadiazole was introduced in condensation reactions with substituted aldehydes to obtain benzylidene imine derivatives (VI)1-5. Further these were treated with sulphanilic acid to give new 2-{[5-phenyl-1,3,4-thiadiazole-2-imino] substituted benzene}diazenyl benzene sulfonic acid derivatives (VII)1-5. These derivatives were further characterized by FT-IR, 1H NMR and 13C NMR spectral studies and were screened for antibacterial, antifungal and antioxidant activities.
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L. Jin, G. Wang, X. Li and L. Li, J. Appl. Electrochem., 41, 377 (2011); https://doi.org/10.1007/s10800-010-0246-z
H.R. Maradiya, J. Serb. Chem. Soc., 67, 709 (2002); https://doi.org/10.2298/JSC0211709M
H. Yan, H. Su, D. Tian, F. Miao and H. Li, Sens. Actuators B Chem., 160, 656 (2011); https://doi.org/10.1016/j.snb.2011.08.044
F. Hipler, R.A. Fischer and J. Muller, Phys. Chem. Chem. Phys., 7, 731 (2005); https://doi.org/10.1039/B415019H
J.F. Dawson, Color. Technol., 9, 25 (1978).
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M.R. De Giorgi, R. Carpignano and A. Cerniani, Dyes Pigments, 37, 187 (1998); https://doi.org/10.1016/S0143-7208(97)00054-5
H. Zollinger, Azo dyes and Pigments. In Color Chemistry: Syntheses, Properties, and Applications of Organic Dyes and Pigments, WileyVCH: Zurich, Switzerland, Ed.: 3, pp. 165–254 (2003).
R. Ullrich and T. Grewer, Thermochim. Acta, 225, 201 (1993); https://doi.org/10.1016/0040 6031(93)80188-G
R. Zhao, C. Tan, Y. Xie, C. Gao, H. Liu and Y. Jiang, Tetrahedron Lett., 52, 3805 (2011); https://doi.org/10.1016/j.tetlet.2011.05.054
T.F. Chung, Y.M. Wu and C.H. Cheng, J. Org. Chem., 49, 1215 (1984); https://doi.org/10.1021/jo00181a015
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C.T. Keerthi Kumar, J. Keshavayya, T.N. Rajesh, S.K. Peethambar and A.R.S. Ali, Org. Chem. Int., 2013, 370626 (2013); https://doi.org/10.1155/2013/370626
A. Kedzia, A. Kudelko, M. Swiatkowski and R. Kruszynski, Dyes Pigments, 172, 107865 (2020); https://doi.org/10.1016/j.dyepig.2019.107865
M. Wróblowska, A. Kudelko, N. Kuznik, K. Laba and M. Lapkowski, J. Heterocycl. Chem., 54, 1550 (2017); https://doi.org/10.1002/jhet.2743
A. Kudelko, M. Wróblowska and M. Lapkowski, Synlett, 26, 2127 (2015); https://doi.org/10.1055/s-0034-1378826
A.T. Mavrova, D. Wesselinova, Y.A. Tsenov and P. Denkova, Eur. J. Med. Chem., 44, 63 (2009); https://doi.org/10.1016/j.ejmech.2008.03.006
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A.W. Bauer, W.M.M. Kirby, J.C. Sherris and M. Turck, Am. J. Clin. Pathol., 45, 493 (1966).
B.W. Williams, M.E. Cuvelier and C. Berset, Lebensm. Wiss. Technol., 28, 25 (1995); https://doi.org/10.1016/S0023-6438(95)80008-5