2,5-DI(HET)ARYLPYRIDINES: SYNTHESIS BY ꞌꞌ1,2,4-TRIAZINEꞌꞌ METHODOLOGY AND PHOTOPHYSICAL PROPERTIES

Authors

  • Alexey P. Krinochkin Ural Federal University named after the first President of Russia B. N. Yeltsin, Institute of Chemical Engineering, 19 Mira St., Ykaterinburg 620002. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620108
  • Albert F. Khasanov Ural Federal University named after the first President of Russia B. N. Yeltsin, Institute of Chemical Engineering, 19 Mira St., Ykaterinburg 620002 https://orcid.org/0000-0002-6742-1737
  • Maria I. Valieva Ural Federal University named after the first President of Russia B. N. Yeltsin, Institute of Chemical Engineering, 19 Mira St., Ykaterinburg 620002. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620108
  • Ekaterina A. Kudryashova Ural Federal University named after the first President of Russia B. N. Yeltsin, Institute of Chemical Engineering, 19 Mira St., Ykaterinburg 620002
  • Mallikarjuna R. Guda Ural Federal University named after the first President of Russia B. N. Yeltsin, Institute of Chemical Engineering, 19 Mira St., Ykaterinburg 620002
  • Dmitry S. Kopchuk Ural Federal University named after the first President of Russia B. N. Yeltsin, Institute of Chemical Engineering, 19 Mira St., Ykaterinburg 620002. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620108
  • Olga V. Shabunina Sirius University of Science and Technology, 1 Olympic Ave., Sirius Federal Territory 354340
  • Nataliya N. Mochulskaya Ural Federal University named after the first President of Russia B. N. Yeltsin, Institute of Chemical Engineering, 19 Mira St., Ykaterinburg 620002
  • Pavel A.Slepukhin Ural Federal University named after the first President of Russia B. N. Yeltsin, Institute of Chemical Engineering, 19 Mira St., Ykaterinburg 620002. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620108
  • Grigory V.Zyryanov Ural Federal University named after the first President of Russia B. N. Yeltsin, Institute of Chemical Engineering, 19 Mira St., Ykaterinburg 620002. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620108
  • Oleg N. Chupakhin Ural Federal University named after the first President of Russia B. N. Yeltsin, Institute of Chemical Engineering, 19 Mira St., Ykaterinburg 620002. Postovsky Institute of Organic Synthesis, Ural Branch of the Russian Academy of Sciences, 22/20 Sofyi Kovalevskoi St., Yekaterinburg 620108

Keywords:

imino ester, pyridine, 1,2,4-triazine, 1,2,4-triazine 4-oxide;, fluorescence, synthesis., aza-Diels-Alder reaction

Abstract

The method for the preparation of 3,6-disubstituted 1,2,4-triazines based on condensation reaction between easily available α-imino esters and isonitrosoacetophenone hydrazones was reported. The significant differences in reaction conditions, ratio of products, and yields between the developed method and the earlier reported approach were demonstrated. The corresponding 2,5-disubstituted pyridines were synthesized from the prepared 1,2,4-triazines, and their photophysical properties were studied. Studies of the photophysical properties revealed low and moderate luminescence quantum yields, and negligible solvatochromic behavior in case of 4-methoxyphenylpyridine derivative due to the role of donating methoxy group, however, with a low linearity of a Lippert–Mataga plot. Nevertheless, 2,5-disubstituted pyridines are of interest due to simple protocols of synthesis, moderate photophysical properties, and potential applicability in different scientific and industrial areas.

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Published

2024-08-01

Issue

Vol. 60 No. 5/6 (2024)

Section

Original Papers