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Electrooxidative thiocyanation and halogenation of azopyrazoles

Anastasia S Kudinova 1
Anastasia S Kudinova
, 
Vera Leonidovna Sigacheva 1
Vera Leonidovna Sigacheva
, 
Boris Vasil'evich Lyalin 1
Boris Vasil'evich Lyalin
, 
Alla G. Tum 1, 2
Alla G. Tum
, 
Natalia V. Gorpinchenko 2
Natalia V. Gorpinchenko
, 
Vladimir Alekseevich Kokorekin 1, 2
Vladimir Alekseevich Kokorekin
, 
Mikhail Petrovich Egorov 1
Mikhail Petrovich Egorov
10.71267/mencom.7938
Published 2026-03-24
Communication , Volume 36, Issue 3, 288-290
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Kudinova A. S. et al. Electrooxidative thiocyanation and halogenation of azopyrazoles // Mendeleev Communications. 2026. Vol. 36. No. 3. pp. 288-290.
GOST all authors (up to 50) Copy
Kudinova A. S., Sigacheva V. L., Lyalin B. V., Tum A. G., Gorpinchenko N. V., Kokorekin V. A., Egorov M. P. Electrooxidative thiocyanation and halogenation of azopyrazoles // Mendeleev Communications. 2026. Vol. 36. No. 3. pp. 288-290.
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TY - JOUR
DO - 10.71267/mencom.7938
UR - https://mendcomm.colab.ws/publications/10.71267/mencom.7938
TI - Electrooxidative thiocyanation and halogenation of azopyrazoles
T2 - Mendeleev Communications
AU - Kudinova, Anastasia S
AU - Sigacheva, Vera Leonidovna
AU - Lyalin, Boris Vasil'evich
AU - Tum, Alla G.
AU - Gorpinchenko, Natalia V.
AU - Kokorekin, Vladimir Alekseevich
AU - Egorov, Mikhail Petrovich
PY - 2026
DA - 2026/03/24
PB - Mendeleev Communications
SP - 288-290
IS - 3
VL - 36
ER -
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@article{2026_Kudinova,
author = {Anastasia S Kudinova and Vera Leonidovna Sigacheva and Boris Vasil'evich Lyalin and Alla G. Tum and Natalia V. Gorpinchenko and Vladimir Alekseevich Kokorekin and Mikhail Petrovich Egorov},
title = {Electrooxidative thiocyanation and halogenation of azopyrazoles},
journal = {Mendeleev Communications},
year = {2026},
volume = {36},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.71267/mencom.7938},
number = {3},
pages = {288--290},
doi = {10.71267/mencom.7938}
}
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Kudinova, Anastasia S., et al. “Electrooxidative thiocyanation and halogenation of azopyrazoles.” Mendeleev Communications, vol. 36, no. 3, Mar. 2026, pp. 288-290. https://mendcomm.colab.ws/publications/10.71267/mencom.7938.
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Keywords

Antifungal activity
azo compounds
bromination
chlorination
electrochemistry
pyrazoles
thiocyanation

Abstract

The anodic C–H functionalization of azopyrazoles [3,3'-(diazenediyl)dipyrazoles] with thiocyanate, bromide, and chloride anions, with or without ZnCl2 as a catalyst, affords the corresponding 4-thiocyanato or 4,4'-dihalo derivatives. The reactions proceed efficiently (56–85% yields) when the oxidation potentials of azopyrazoles and the anions (or their ZnII complexes) differentiate in ~0.1–0.6 V, so the iodo products are not formed. The products bearing SCN group possess antifungal activity, likely via inhibiting ergosterol biosynthesis, with the azo group enhancing this effect.

Funders

Russian Science Foundation
25-23-00447

References

2.
ref-10.71267-mendc7442-1-2-1-0
2003
4.
Trinitromethyl-substituted 5-nitro- or 3-azo-1,2,4-triazoles: synthesis, characterization, and energetic properties.
Thottempudi V., Gao H., Shreeve J.M.
Journal of the American Chemical Society, 2011
6.
Electrooxidation Is a Promising Approach to Functionalization of Pyrazole-Type Compounds
Lyalin B.V., Sigacheva V.L., Kudinova A.S., Neverov S.V., Kokorekin V.A., Petrosyan V.A.
Molecules, 2021
7.
ref-10.71267-mendc7442-1-7-1-0
A. S. Kudinova, E. D. Siling, N. V. Gorpinchenko, V. L. Sigacheva, B. V. Lyalin and V. A. Kokorekin
Vestnik RFFI, 2024
8.
Electrooxidative Thiocyanation of Hydroxy‐ and Alkoxybenzenes
Moiseeva N.V., Sokolov A., Andreev I., Ratmanova N., Trushkov I., Kokorekin V.
European Journal of Organic Chemistry, 2024
10.
Electrochemical halogenation of organic compounds
Lyalin B.V., Petrosyan V.A.
Russian Journal of Electrochemistry, 2013
11.
ref-10.71267-mendc7442-1-11-1-0
N. A. Semina, S. V. Sidorenko, S. P. Rezvan, S. L. Grudinina, L. S. Strachunsky, O. U. Stetciuk, R. S. Kozlov, M. V. Eidel'shtein, E. A. Ved'mina, L. G. Stolyarova, I. V. Vlasova and Z. S. Sereda
Klin. Mikrobiol. Antimikrob. Khimioter., 2004
12.
EUCAST Definitive Document EDef 7.1: method for the determination of broth dilution MICs of antifungal agents for fermentative yeasts: Subcommittee on Antifungal Susceptibility Testing (AFST) of the ESCMID European Committee for Antimicrobial Susceptibility Testing (EUCAST)∗
Rodriguez-Tudela J.L., Arendrup M.C., Barchiesi F., Bille J., Chryssanthou E., Cuenca-Estrella M., Dannaoui E., Denning D.W., Donnelly J.P., Dromer F., Fegeler W., Lass-Flörl C., Moore C., Richardson M., Sandven P., et. al.
Clinical Microbiology and Infection, 2008
13.
ref-10.71267-mendc7442-1-13-1-0
2017
14.
ref-10.71267-mendc7442-1-14-1-0
2020
15.
Prediction of the Biological Activity Spectra of Organic Compounds Using the Pass Online Web Resource
Filimonov D.A., Lagunin A.A., Gloriozova T.A., Rudik A.V., Druzhilovskii D.S., Pogodin P.V., Poroikov V.V.
Chemistry of Heterocyclic Compounds, 2014
16.
Antifungal activity of 5 new synthetic compounds vs. Trichophyton rubrum and Epidermophyton floccosum
Romagnoli C., Mares D., Bruni A., Andreotti E., Manfrini M., Vicentini C.B.
Mycopathologia, 2002