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Completely Regioselective N-Tosylation of 5-Acetyl-4-aryl-6-hydroxy-3,6-dimethyl-4,5,6,7-tetrahydroindazoles

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Abstract

The reaction of 5-acetyl-4-aryl-6-hydroxy-3,6-dimethyl-4,5,6,7-tetrahydroindazoles p-toluenesulfonyl chloride in boiling acetone in the presence of triethylamine was found to occur in a completely regioselective with the exclusive formation of 5-acetyl-4-aryl-6-hydroxy-3,6-dimethyl-1-(4-methylbenzenesulfonyl)-4,5,6,7-tetrahydroindazoles. The experimental results were confirmed by quantum chemical calculations. In silico biological activity evaluation of the synthesized compounds was performed.

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Funding

This study was performed under financial support by the Ministry of Science and Higher Education of the Russian Federation (project no. 0795-2020-0010, V.V. Dotsenko).

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Authors and Affiliations

  1. Baku State University, 1148, Baku, Azerbaijan

    A. I. Ismiyev & A. M. Maharramov

  2. Kuban State University, 350040, Krasnodar, Russia

    V. V. Dotsenko & A. V. Bespalov

  3. North Caucasus Federal University, 355009, Stavropol, Russia

    V. V. Dotsenko

  4. Taurida Academy, Vernadsky Crimean Federal University, 295007, Simferopol, Russia

    E. E. Netreba

Authors
  1. A. I. Ismiyev
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  2. V. V. Dotsenko
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  3. A. V. Bespalov
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  4. E. E. Netreba
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  5. A. M. Maharramov
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Correspondence to V. V. Dotsenko.

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Ismiyev, A.I., Dotsenko, V.V., Bespalov, A.V. et al. Completely Regioselective N-Tosylation of 5-Acetyl-4-aryl-6-hydroxy-3,6-dimethyl-4,5,6,7-tetrahydroindazoles. Russ J Gen Chem 90, 187–195 (2020). https://doi.org/10.1134/S1070363220020048

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