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Electrocatalytic Cascade Reaction of Aldehydes and 4-Hydroxy-6-methyl-2H-pyran-2-one

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Abstract

The electrolysis of salicylaldehydes and 4-hydroxy-6-methyl-2H-pyran-2-one in an undivided cell in alcoholic media and in the presence of alkali metal halides results in rapid and efficient formation of the substituted 3-acetoacetylcoumarins in 85–93% product yields and 425–930% current efficiency. This novel chain electrocatalytic process reveals a “green” and advantageous route to functionalized 3-acetoacetylcoumarins having promising properties for the different biomedical and other practical applications. The analogous process with arylaldehydes leads to substituted 3,3′-(arylmethylene)bis(4-hydroxy-6-methyl-2H-pyran-2-ones). Thus, under mild conditions, this simple electrocatalytic system produces the electrochemically induced Knoevenagel condensation of aldehydes and 6-methyl-2H-pyran-2-one with either subsequent rearrangement in case of salicylaldehydes towards 3-acetoacetylcoumarins or further addition of 6-methyl-2H-pyran-2-one molecule in case of arylaldehydes, leading to substituted 3,3′-(arylmethylene)bis(4-hydroxy-6-methyl-2H-pyran-2-ones).

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Funding

M. N. E. thanks the University of Alcala for the “Giner de los Rios” financial support. The study was financially supported by the University of Alcala (project no. CCGP2017/EXP-009) and the Council at President of the Russian Federation (project MD-380.2017.3).

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Authors and Affiliations

  1. N. D. Zelinsky Institute of Organic Chemistry, Leninsky Prospect 47, Moscow, Russia, 119991

    Michail N. Elinson, Olga O. Sokolova & Alexander D. Korshunov

  2. Department of Organic Chemistry and Inorganic Chemistry, University of Alcalá, 28871, Alcalá de Henares, Madrid, Spain

    Fructuoso Barba & Belen Batanero

  3. Instituto de Investigación Química “Andrés M. del Río” (IQAR), University of Alcalá, 28871, Alcalá de Henares, Madrid, Spain

    Belen Batanero

Authors
  1. Michail N. Elinson
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  2. Olga O. Sokolova
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  3. Alexander D. Korshunov
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  4. Fructuoso Barba
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  5. Belen Batanero
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Correspondence to Michail N. Elinson.

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Elinson, M.N., Sokolova, O.O., Korshunov, A.D. et al. Electrocatalytic Cascade Reaction of Aldehydes and 4-Hydroxy-6-methyl-2H-pyran-2-one. Electrocatalysis 9, 602–607 (2018). https://doi.org/10.1007/s12678-018-0470-6

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  • DOI: https://doi.org/10.1007/s12678-018-0470-6

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