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3,4,5,6-Tetrafluoro-1,2-dehydrobenzene in reactions with 1,2,4-triazines

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Abstract

Tetrafluoro-substituted aryne, 3,4,5,6-tetrafluoro-1,2-dehydrobenzene, has been generated in situ from 2-amino-3,4,5,6-tetrafluorobenzoic acid, and its reactivity in reactions with 1,2,4-triazines as dienes has been studied. In these reactions, the corresponding azine ring transformation products, i.e., 1,2,3,4-tetrafluoro-10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indoles, have been obtained, in the case of triazines activated by the presence of electron-withdrawing groups, such as 6-aryl-3-(2-pyridyl)-5-cyano-1,2,4-triazines. The crystal structure of the obtained products was confirmed by X-ray diffraction analysis.

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Acknowledgements

This work was supported by the Russian Science Foundation (Grant # 15-13-10033), the Council for grants of the President of the Russian Federation (Grant No. MK-3079.2015.3) and Act # 211 of Russian Federation Government (No. 02.A03.21.0006).

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Authors and Affiliations

  1. Ural Federal University, 19, Mira St., Yekaterinburg, Russian Federation, 620002

    Dmitry S. Kopchuk, Nikolay V. Chepchugov, Eugeny B. Gorbunov, Grigory V. Zyryanov, Igor S. Kovalev, Emiliya V. Nosova, Pavel A. Slepukhin, Vladimir L. Rusinov & Oleg N. Chupakhin

  2. Postovsky Institute of Organic Synthesis of RAS (Ural Division), 22/20 S. Kovalevskoy/Akademicheskaya St., Yekaterinburg, Russian Federation, 620990

    Dmitry S. Kopchuk, Eugeny B. Gorbunov, Grigory V. Zyryanov, Emiliya V. Nosova, Pavel A. Slepukhin, Vladimir L. Rusinov & Oleg N. Chupakhin

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  1. Dmitry S. Kopchuk
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Correspondence to Emiliya V. Nosova.

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Kopchuk, D.S., Chepchugov, N.V., Gorbunov, E.B. et al. 3,4,5,6-Tetrafluoro-1,2-dehydrobenzene in reactions with 1,2,4-triazines. J IRAN CHEM SOC 14, 1507–1512 (2017). https://doi.org/10.1007/s13738-017-1091-3

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