Abstract
New substituted 5,6-dihydro[1,2,4]triazolo[4,3-a][1,3,5]triazines were synthesized by cyclocondensation of N-alkyl(aryl)-N′-(4H-1,2,4-triazol-3-yl)ethan- and -propanimidamides with benzaldehyde or ethyl methyl ketone in the presence of p-toluenesulfonic acid in 1,4-dioxane under reflux. The reaction tolerated a broad substrate scope and provided good yields (43–64%). The structure of the newly synthesized compounds was confirmed by elemental analyses and IR, 1H and 13C NMR, and mass spectra.
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Najm, M.A.A., Serya, R.A.T., and Abouzid, Kh.A.M., Am. J. Sci., 2017, vol. 13, p. 74. doi 10.7537/marsjas130317.08
Fischer, G., Adv. Heterocycl. Chem., 1993, vol. 57, p. 81. doi 10.1016/S0065-2725(08)60887-9
Topp, E., Mulbry, W.M., Zhu, H., Nour, S.M., and Cuppels, D., Appl. Environ. Microbiol., 2000, vol. 66, p. 3134. doi 10.1128/AEM.66.8.3134-3141.2000
Akahoshi, F., Takeda, S., Okada, T., Kajii, M., Nishimura, H., Sugiura, H. M., Inoue, Y., Fukaya, C., Naito, Y., Imagawa, T., and Nakamura, N., J. Med. Chem., 1998, vol. 41, p. 2985. doi 10.1021/jm970759u
Zhan, Z., Peng, X., Chen, F., Ji, Y., Yao, S., Xi, Y., Lin, Y., Chen, T., Xu, Y., Ai, J., Geng, M., and Duan, W., Eur. J. Med. Chem., 2016, vol. 116, p. 239. doi10.1016/j.ejmech.2016.03.076
Gomha, S.M., Khalil, K.D., El- Zanaty, A.M., and Riyadh, S.M., Heterocycles, 2013, vol. 87, p. 1109. doi 10.3987/COM-13-12696
Patel, B.D., Bhadada, S.V., and Ghate, M.D., Bioorg. Chem., 2017, vol. 72, p. 345. doi 10.1016/j.bioorg.2017.03.004
Abderrahim, R., Phosphorus, Sulfur Silicon Relat. Elem., 2006, vol. 181, p. 581. doi 10.1080/10426500500269380
Hajri, A. and Marzouki, M.L., Heterocycl. Commun., 2017, vol. 23, p. 97. doi 10.1515/hc-2017-0003
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Hajri, A., Marzouki, L. Easy Strategy for the Synthesis of New 5,6-Dihydro-[1,2,4]triazolo[4,3-a][1,3,5]triazine Derivatives. Russ J Org Chem 55, 1394–1398 (2019). https://doi.org/10.1134/S1070428019090203
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DOI: https://doi.org/10.1134/S1070428019090203