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Azolyl-substituted 1,2,3-triazoles

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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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Authors and Affiliations

  1. Togliatti State University, ul. Belorusskaya 14, Togliatti, 445667, Russia

    A. A. Golovanov, I. S. Odin & V. V. Bekin

  2. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, ul. Vavilova 28, Moscow, 119991, Russia

    A. V. Vologzhanina & I. S. Bushmarinov

  3. Ufa State Petroleum Technological University, ul. Kosmonavtov 1, Ufa, 450062, Bashkortostan, Russia

    S. S. Zlotskii

  4. Korolev Samara State Aerospace University, Moskovskoe shosse 34, Samara, 443086, Russia

    Yu. L. Gerasimov & P. P. Purygin

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  1. A. A. Golovanov
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  2. I. S. Odin
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  3. V. V. Bekin
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  4. A. V. Vologzhanina
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  5. I. S. Bushmarinov
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  6. S. S. Zlotskii
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  7. Yu. L. Gerasimov
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  8. P. P. Purygin
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Correspondence to A. A. Golovanov.

Additional information

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

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