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Transformations of 6-[4-(methylthio)phenyl]-3-(2-pyridyl)-1,2,4-triazines in the reaction with an aryne intermediate

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Abstract

Transformations of the various 6-[4-(methylthio)phenyl]-3-(2-pyridyl)-1,2,4-triazines in their reactions with an aryne intermediate were investigated. It was shown that the interaction of a 5-unsubstituted triazine with the aryne led to an S-arylation product, whereas there were no any transformations of the pyridyltriazine system. Introduction of the pentafluorophenyl substituent at the C(6) position of the triazine changed the pathway in this reaction with the aryne, which proceeded simultaneously at two reaction centers. In particular, there were a rearrangement of the 3-(2-pyridyl)-1,2,4-triazine into the 10-(1H-1,2,3-triazol-1-yl)pyrido[1,2-a]indole system as well as S-arylation. The product of dual functionalization, 10-{5-perfluorophenyl-4-[4-(phenylthio)phenyl]-1H-1,2,3-triazol-1-yl}pyrido[1,2-a]indole, exhibited a blue emission at λem = 395 nm and a fluorescence quantum yield comparable to the analogs obtained previously.

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Funding

This work was financially supported by the Russian Science Foundation (Project No. 20-73-10077; https://rscf.ru/en/project/20-73-10077/).

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Authors and Affiliations

  1. Ural Federal University named after the first President of Russia B. N. Yeltsin, 19 ul. Mira, 620002, Yekaterinburg, Russian Federation

    T. D. Moseev, T. A. Idrisov, I. A. Lavrinchenko, A. P. Krinochkin, E. A. Kudryashova, D. S. Kopchuk, M. V. Varaksin, G. V. Zyryanov, V. N. Charushin & O. N. Chupakhin

  2. I. Ya. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 ul. S. Kovalevskoy, 620137, Yekaterinburg, Russian Federation

    A. P. Krinochkin, D. S. Kopchuk, M. V. Varaksin, G. V. Zyryanov, V. N. Charushin & O. N. Chupakhin

Authors
  1. T. D. Moseev
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  2. T. A. Idrisov
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  3. I. A. Lavrinchenko
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  4. A. P. Krinochkin
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  5. E. A. Kudryashova
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  6. D. S. Kopchuk
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  7. M. V. Varaksin
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  8. G. V. Zyryanov
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  9. V. N. Charushin
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  10. O. N. Chupakhin
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Corresponding author

Correspondence to M. V. Varaksin.

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No human or animal subjects were used in this research.

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The authors declare no competing interests.

Additional information

Based on the materials of the VII International Conference “Modern Synthetic Methodologies for Creating Drugs and Functional Materials” (MOSM 2023) dedicated to the 125th birth anniversary of Academician I. Ya. Postovsky (September 10–16, 2023, Yekaterinburg—Perm, Russia).

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 12, pp. 2922–2926, December, 2023.

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Moseev, T.D., Idrisov, T.A., Lavrinchenko, I.A. et al. Transformations of 6-[4-(methylthio)phenyl]-3-(2-pyridyl)-1,2,4-triazines in the reaction with an aryne intermediate. Russ Chem Bull 72, 2922–2926 (2023). https://doi.org/10.1007/s11172-023-4102-9

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  • DOI: https://doi.org/10.1007/s11172-023-4102-9

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