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Di-tert-alkyl-substituted catechols with an imidazole substituent: synthesis, structure, and properties

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Abstract

Di-tert-alkyl-substituted catechols with a heterocyclic imidazole-type substituent were synthesized in three steps from catecholaldehydes. The 1,1,4,4-tetramethylbutanediyl substituent was shown to be resistant to the action of acids in the demethylation reaction. The isomerization of 3,4,5-substituted catechols to the 3,4,6-substituted isomers was observed. The molecular structures of the synthesized compounds in the crystalline state were established by X-ray diffraction analysis. For the catechol derivatives, the tertiary substituent in the ortho position to the imidazole moiety was shown to have an effect on the mutual arrangement of the catechol and heterocyclic moieties. The electrochemical properties of the synthesized imidazole-containing catechols were studied and their anti-radical activity was evaluated by the 2,2-diphenyl-1-picrylhydrazyl assay.

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Authors and Affiliations

  1. G. A. Razuvaev Institute of Organometallic Chemistry, Russian Academy of Sciences, 49 ul. Tropinina, 603950, Nizhny Novgorod, Russian Federation

    M. A. Zherebtsov, M. V. Arsenyev, N. M. Khamaletdinova, E. V. Baranov & S. A. Chesnokov

  2. N. I. Lobachevsky State University of Nizhny Novgorod, 23 prosp. Gagarina, 603950, Nizhny Novgorod, Russian Federation

    M. A. Zherebtsov & M. V. Arsenyev

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  1. M. A. Zherebtsov
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  2. M. V. Arsenyev
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  3. N. M. Khamaletdinova
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  4. E. V. Baranov
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Correspondence to M. V. Arsenyev.

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This study was financially supported by the Russian Science Foundation (Project No. 19-73-10173-P). The studies were performed using the equipment of the Center for Collective Use “Analytical Center of the G. A. Razuvaev Institute of Organometallic Chemistry of the Russian Academy of Sciences” with the financial support of the Ministry of Science and Higher Education (Grant “Ensuring the Development of the Material and Technical Infrastructure of the Centers for Collective Use of Scientific Equipment,” unique identifier RF-2296.61321X0017, agreement number 075-15-2021-670).

No human or animal subjects were used in this research.

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, Vol. 72, No. 9, pp. 2102–2118, September, 2023.

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Zherebtsov, M.A., Arsenyev, M.V., Khamaletdinova, N.M. et al. Di-tert-alkyl-substituted catechols with an imidazole substituent: synthesis, structure, and properties. Russ Chem Bull 72, 2102–2118 (2023). https://doi.org/10.1007/s11172-023-4005-9

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