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Electrosynthesis of 4-iodopyrazole and its derivatives

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Abstract

Electrosynthesis of 4-iodo-substituted pyrazoles has been accomplished by iodination of the corresponding precursors on a Pt-anode in aqueous solutions of KI under conditions of the diaphragm galvanostatic electrolysis. Efficiency of the process depends on the donor-acceptor properties of substituents and their positions in the pyrazole ring. Thus, iodination of pyrazole, 3,5-dimethylpyrazole, 3-nitropyrazole, 1-methylpyrazole, 1,3-dimethylpyrazole, pyrazole-3(5)-carboxylic acid or methyl esters furnished 4-iodo derivatives in 57, 86, 2, 5, 35, 30, and 40% yields, respectively.

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, 47 Leninsky prosp., 119991, Moscow, Russian Federation

    B. V. Lyalin, V. A. Petrosyan & B. I. Ugrak

Authors
  1. B. V. Lyalin
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  2. V. A. Petrosyan
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  3. B. I. Ugrak
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Corresponding author

Correspondence to V. A. Petrosyan.

Additional information

Published in Russian in Izvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1512–1518, August, 2010.

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Lyalin, B.V., Petrosyan, V.A. & Ugrak, B.I. Electrosynthesis of 4-iodopyrazole and its derivatives. Russ Chem Bull 59, 1549–1555 (2010). https://doi.org/10.1007/s11172-010-0277-y

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  • DOI: https://doi.org/10.1007/s11172-010-0277-y

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