Abstract
Huisgen reaction of (E)-1,5-diarylpent-2-en-4-yn-1-ones and (E)-1,5-diarylpent-1-en-4-yn-3-ones afforded 1-aryl-3-(5-aryl-1H-1,2,3-triazol-4-yl)prop-2-en-1-ones and 3-aryl-1-(5-aryl-1H-1,2,3-triazol-4-yl)-prop-2-en-1-ones, respectively. (E)-1-Aryl-3-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-ones reacted with hydrazine hydrate and phenylhydrazine to give 72–93% of 4-(3-aryl-4,5-dihydro-1H-pyrazol-5-yl)-5-phenyl-1H-1,2,3-triazoles which underwent dehydrogenation on heating in boiling acetic acid with formation of the corresponding pyrazole derivatives. The molecular structures of (E)-3-phenyl-1-(5-phenyl-1H-1,2,3-triazol-4-yl)prop-2-en-1-one and 4-[3-(4-methylphenyl)-1-phenyl-4,5-dihydro-1H-pyrazol-5-yl]-5-phenyl-1H-1,2,3-triazole were studied by X-ray analysis. 4-(3-Aryl-4,5-dihydro-1H-pyrazol-5-yl)-5-phenyl-1H-1,2,3-triazoles showed toxicity against Daphnia magna.
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Lauria, A., Delisi, R., Mingoia, F., Terenzi, A., Martorana, A., Barone, G., and Almerico, A.M., Eur. J. Org. Chem., 2014, p. 3289.
Oliva, C.G., Jagerovic, N., Goya, P., Alkorta, I., Elguero, J., Cuberes, R., and Dordal, A., Arkivoc, 2010, part (ii), p. 127.
Cheng, H., Wan, J., Lin, M.I., Liu, Y., Lu, X., Chen, J., Tu, Z., Cheng, Y.-S.E., and Ding, K., J. Med. Chem., 2012, vol. 55, p. 2144.
Pardin, C., Roy, I., Lubell, W.D., and Keillor, J.K., Chem. Biol. Drug Des., 2008, vol. 72, p. 189.
Pardin, C., Pelletier, J.N., Lubell, W.D., and Keillor, J.K., J. Org. Chem., 2008, vol. 73, p. 5766.
Chebanov, V.A., Desenko, S.M., and Gurley, T.W., Azaheterocycles Based on a,ß-Unsaturated Carbonyls, Berlin: Springer, 2008, p. 210.
Dong, H.S., Wang, H.C., Gao, Z.L., Li, R.S., and Cui, F.H., J. Heterocycl. Chem., 2010, vol. 47, p. 389.
Shanmugavelan, P., Nagarajan, S., Sathishkumar, M., Ranganathan, R., and Ponnuswamy, A., Lett. Org. Chem., 2014, vol. 11, p. 446.
Dong, W.J., Cui, F.H., Gao, Z.L., Li, R.S., Chen, G.L., and Dong, H.S., J. Heterocycl. Chem., 2011, vol. 48, p. 1154.
Abdel-Wahab, B.F., Abdel-Latif, E., Mohamed, H.A., and Awad, G.E.A., Eur. J. Med. Chem., 2012, vol. 52, p. 263.
Nagarajan, S., Shanmugavelan, P., Sathishkumar, M., Selvi, R., Ponnuswamy, A., Harikrishnan, H., and Shanmugaiah, V., Chin. Chem. Lett., 2014, vol. 25, p. 146.
Migliorese, K.G., Nanaka, Y., and Miller, S.I., J. Org. Chem., 1974, vol. 39, p. 739.
Golovanov, A.A. and Odin, I.S., Russ. J. Org. Chem., 2015, vol. 51, p. 447.
Krivolapov, V.P. and Shkurko, O.P., Russ. Chem. Rev., 2005, vol. 74, p. 339.
Journet, M., Cai, D., Kowal, J.J., and Larsen, R.D., Tetrahedron Lett., 2001, vol. 43, p. 9117.
Verkhozina, O.N., Kizhnyaev, V.N., Vereshchagin, L.I., Rokhin, A.V., and Smirnov, A.I., Russ. J. Org. Chem., 2003, vol. 39, p. 1792.
Ferreria, J.P.A., Silva, V.L.M., Silva, J.E., and Silva, A.M.S., Tetrahedron Lett., 2013, vol. 54, p. 5391.
Grigor’ev, V.Yu., Razdol’skii, V.Yu., Zagrebin, A.O., Tonkopii, V.D., and Raevskii, O.A., Pharm. Chem. J., 2014, vol. 48, p. 242.
TOPAS 4.2 User Manual, Karlsruhe, Germany Bruker AXS, 2009.
Coelho, A.A., J. Appl. Crystallogr., 2003, vol. 36, p. 86.
Favre-Nicolin, V. and Cerný, R., J. Appl. Crystallogr., 2002, vol. 35, p. 734.
Bushmarinov, I.S., Dmitrienko, A.O., Korlyukov, A.A., and Antipin, M.Y., J. Appl. Crystallogr., 2012, vol. 45, p. 1187.
Cheary, R., Coelho, A., and Cline, J., J. Res. Natl. Inst. Stand. Technol., 2004, vol. 109, p. 1.
Sheldrick, G.M., SADABS v. 2.01, Bruker/Siemens Area Detector Absorption Correction Program, Madison, Wisconsin, USA Bruker AXS, 1998.
Spek, A.L., Acta Crystallogr., Sect. D, 2009, vol. 65, p. 148.
Sheldrick, G.M., Acta Crystallogr., Sect. A, 2008, vol. 64, p. 112.
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J., Howard, J.A.K., and Puschmann, H., J. Appl. Crystallogr., 2009, vol. 42, p. 339.
Golovanov, A.A., Latypova, D.R., Bekin, V.V., Pisareva, V.S., Vologzhanina, A.V., and Dokichev, V.A., Russ. J. Org. Chem., 2013, vol. 49, p. 1264.
Utekhina, N.V., Korzhova, N.V., Kazantseva, V.M., Surov, Yu.N., Orlov, V.D., and Korshunov, S.P., Russ. J. Gen. Chem., 1988, vol. 58, p. 612.
Stroganov, N.S., Metodiki biologicheskikh issledovanii po vodnoi toksikologii (Biological Tests in Water Toxicology), Moscow: Nauka, 1971, p. 14.
Gubler, E.V., Vychislitel’nye metody analiza i raspoznavaniya patologicheskikh protsessov (Computational Methods for Analysis and Recognition of Pathological Processes), Leningrad: Meditsina, 1978, p. 294.
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Original Russian Text © A.A. Golovanov, I.S. Odin, V.V. Bekin, A.V. Vologzhanina, I.S. Bushmarinov, S.S. Zlotskii, Yu.L. Gerasimov, P.P. Purygin, 2016, published in Zhurnal Organicheskoi Khimii, 2016, Vol. 52, No. 3, pp. 434–440.
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Golovanov, A.A., Odin, I.S., Bekin, V.V. et al. Azolyl-substituted 1,2,3-triazoles. Russ J Org Chem 52, 414–420 (2016). https://doi.org/10.1134/S1070428016030209
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DOI: https://doi.org/10.1134/S1070428016030209