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Mendeleev Communications, 2019, Volume 29, Issue 3, Pages 334–336
DOI: https://doi.org/10.1016/j.mencom.2019.05.032
(Mi mendc1515)
 

This article is cited in 18 scientific papers (total in 18 papers)

Communications

Double electrooxidative C–H functionalization of (het)arenes with thiocyanate and 4-nitropyrazolate ions

R. R. Yaubasarovaa, V. A. Kokorekinabc, G. V. Ramenskayab, V. A. Petrosyana

a N.D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Moscow, Russian Federation
b I.M. Sechenov First Moscow State Medical University, Moscow, Russian Federation
c All-Russian Research Institute of Phytopathology, Bol'shiye Vyazemy, Moscow Region, Russian Federation
Abstract: The double anodic C–H functionalization of N-methyl-1H-pyrrole and N,N-dimethylaniline using both thiocyanate and 4-nitro-1H-pyrazolate ions as nucleophiles has been accomplished for the first time. The mild reaction conditions and considerable pharmacological activity of the target products make such C–S and C–N coupling strategy to be highly attractive for further applications.
Document Type: Article
Language: English


Citation: R. R. Yaubasarova, V. A. Kokorekin, G. V. Ramenskaya, V. A. Petrosyan, “Double electrooxidative C–H functionalization of (het)arenes with thiocyanate and 4-nitropyrazolate ions”, Mendeleev Commun., 29:3 (2019), 334–336
Linking options:
  • https://www.mathnet.ru/eng/mendc1515
  • https://www.mathnet.ru/eng/mendc/v29/i3/p334
  • This publication is cited in the following 18 articles:
    1. Chang-Sheng Wang, Yuan Xu, Shao-Peng Wang, Chun-Ling Zheng, Guowei Wang, Qiao Sun, “Recent advances in selective mono-/dichalcogenation and exclusive dichalcogenation of C(sp2)–H and C(sp3)–H bonds”, Org. Biomol. Chem., 22:4 (2024), 645  crossref
    2. Y. N. Kozyrev, A. S. Mendkovich, V. A. Kokorekin, V. B. Luzhkov, A. I. Rusakov, V. V. Jouikov, “The Effect of Proton Donors on the Process of Electrochemical Generation of Thiocyanogen and Its Reactivity”, Russ J Electrochem, 60:12 (2024), 1028  crossref
    3. Jawher Makhlouf, Youness El Bakri, Kandasamy Saravanan, Arto Valkonen, Wajda Smirani, “Self-assembly, physico-chemical characterization, biological, virtual screening, and computational approach of novel 2-amino pyridine derivatives”, Journal of Molecular Structure, 1281 (2023), 135049  crossref
    4. Boris V. Lyalin, Vera L. Sigacheva, Anastasia S. Kudinova, Bogdan I. Ugrak, Vladimir A. Petrosyan, Vladimir A. Kokorekin, “Electrooxidative N–N Cross Coupling: A Way to New Azopyrazoles”, Chem Heterocycl Comp, 58:1 (2022), 1  crossref
    5. Pran Gopal Karmaker, Md. Asraful Alam, Feng Huo, “Recent advances in photochemical and electrochemically induced thiocyanation: a greener approach for SCN-containing compound formation”, RSC Adv., 12:10 (2022), 6214  crossref
    6. O. M. Mulina, O. V. Bityukov, V. A. Vil', A. O. Terent'ev, “Photo- and Electrochemically Initiated Thiocyanation Reactions”, Russ J Org Chem, 58:12 (2022), 1712  crossref
    7. Oleg V. Bityukov, Andrey S. Kirillov, Pavel Yu. Serdyuchenko, Maria A. Kuznetsova, Valentina N. Demidova, Vera A. Vil', Alexander O. Terent'ev, “Electrochemical thiocyanation of barbituric acids”, Org. Biomol. Chem., 20:17 (2022), 3629  crossref
    8. V. M. Khodonov, A. S. Kudinova, V. A. Kokorekin, V. A. Petrosyan, M. P. Egorov, “Effective metal-free electrooxidative thiocyanation of anilines”, Mendeleev Commun., 32:1 (2022), 94–96  mathnet  crossref
    9. V. A. Kokorekin, V. M. Khodonov, S. V. Neverov, N. É. Grammatikova, V. A. Petrosyan, ““Metal-free” synthesis and antifungal activity of 3-thiocyanatopyrazolo[1,5-a]pyrimidines”, Russ Chem Bull, 70:3 (2021), 600  crossref
    10. Boris V. Lyalin, Vera L. Sigacheva, Anastasia S. Kudinova, Sergey V. Neverov, Vladimir A. Kokorekin, Vladimir A. Petrosyan, “Electrooxidation Is a Promising Approach to Functionalization of Pyrazole-Type Compounds”, Molecules, 26:16 (2021), 4749  crossref
    11. Yuriy N. Kozyrev, Andrey S. Mendkovich, Vladimir A. Kokorekin, Victor B. Luzhkov, Alexander I. Rusakov, “Integrated Study of the Thiocyanate Anion Electrooxidation by Electroanalytical and Computational Methods”, J. Electrochem. Soc., 168:12 (2021), 125501  crossref
    12. Mandeep Kaur Hunjan, Surabhi Panday, Anjali Gupta, Jayeeta Bhaumik, Parthasarathi Das, Joydev K. Laha, “Recent Advances in Functionalization of Pyrroles and their Translational Potential”, The Chemical Record, 21:4 (2021), 715  crossref
    13. Mikhail Yu. Sharipov, Igor B. Krylov, Ivan D. Karpov, Olga V. Vasilkova, Anna-Maria V. Oleksiienko, Alexander O. Terent'ev, “NaSCN–(NH4)2Ce(NO3)6 system in heterocycle thiocyanation: synthesis of novel highly potent broad-spectrum fungicides for crop protection”, Chem Heterocycl Comp, 57:5 (2021), 531  crossref
    14. Oleg N. Chupakhin, Alexander V. Shchepochkin, Valery N. Charushin, Advances in Heterocyclic Chemistry, 131, 2020, 1  crossref
    15. Vladimir A. Kokorekin, Sergey V. Neverov, Vera N. Kuzina, Vladimir A. Petrosyan, “A New Method for the Synthesis of 3-Thiocyanatopyrazolo[1,5-a]pyrimidines”, Molecules, 25:18 (2020), 4169  crossref
    16. D. A. Burmistrova, I. V. Smolyaninov, N. T. Berberova, “Directed oxidative coupling of thiols in the synthesis of unsymmetrical disulfides”, Russ Chem Bull, 69:5 (2020), 990  crossref
    17. V. A. Kokorekin, E. I. Melnikova, R. R. Yaubasarova, V. A. Petrosyan, “Electrooxidative C–H thiocyanation of hetarenes: voltammetric assessment of thiocyanogen reactivity”, Mendeleev Commun., 30:1 (2020), 70–72  mathnet  crossref
    18. V. A. Kokorekin, E. I. Mel'nikova, R. R. Yaubasarova, N. V. Gorpinchenko, V. A. Petrosyan, ““Metal-free” electrooxidative C—H thiocyanation of arenes”, Russ Chem Bull, 68:11 (2019), 2140  crossref
    Citing articles in Google Scholar: Russian citations, English citations
    Related articles in Google Scholar: Russian articles, English articles
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