Abstract:
Electrocatalytic transformation of aldehydes, 2,4-dihydro-3H-pyrazol-3-ones and kojic acid in alcohols occurs in an undivided cell in the presence of sodium halides, selectively affording substituted 4-{[3-hydroxy-6-(hydroxymethyl)-4-oxo-4H-pyran-2-yl](aryl)methyl}-5-methyl-1,2-dihydro-3Hpyrazol-3-ones in 73–95% yields and with 240–320% current efficiency. The multicomponent process provides a facile and efficient way to the new type of systems with heterocyclic moieties separated by aryl-substituted C-spacer. The product structure has been confirmed by X-ray diffraction data
Keywords:
electrocatalysis, multicomponent process, tandem reaction, aldehydes, 2,4-dihydro-3H-pyrazol-3-one, kojic acid.
Citation:
M. N. Elinson, A. N. Vereshchagin, Yu. E. Ryzhkova, S. K. Krymov, N. A. Leonova, A. S. Goloveshkin, M. P. Egorov, “Electrocatalytic one-pot multicomponent assembly of aldehydes, 2,4-dihydro-3H-pyrazol-3-ones and kojic acid”, Mendeleev Commun., 30:2 (2020), 223–225
Linking options:
https://www.mathnet.ru/eng/mendc1155
https://www.mathnet.ru/eng/mendc/v30/i2/p223
This publication is cited in the following 7 articles:
Michail N. Elinson, Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Alexander O. Chizhov, Mikhail P. Egorov, “Multicomponent Assembling of Aldehydes, N,N‐Dimethylbarbituric Acid, Malononitrile, and Morpholine Into Unsymmetrical Ionic Scaffold and Its Efficient Cyclization”, Journal of Heterocyclic Chem, 61:11 (2024), 1752
M. N. Elinson, A. N. Vereshchagin, Yu. E. Ryzhkova, F. V. Ryzhkov, “Electrochemical transformations of CH-acids”, Mendeleev Commun., 34:2 (2024), 145–155
Yuliya E. Ryzhkova, Varvara M. Kalashnikova, Fedor V. Ryzhkov, Michail N. Elinson, “5-(1-(4-Hydroxy-6-methyl-2-oxo-2H-pyran-3-yl)-2-oxo-2-phenylethyl)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione”, Molbank, 2023:2 (2023), M1640
M. N. Elinson, A. N. Vereshchagin, Y. E. Ryzhkova, K. A. Karpenko, I. E. Ushakov, O. I. Maslov, M. P. Egorov, “Four-component transformation of benzaldehydes, dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one, and morpholine into the unsymmetrical ionic scaffold with three different heterocyclic rings”, Russ Chem Bull, 71:3 (2022), 464
Fedor V. Ryzhkov, Michail N. Elinson, Yuliya E. Ryzhkova, Anatoly N. Vereshchagin, Victor A. Korolev, Mikhail P. Egorov, “Pseudo‐four‐component synthesis and in silico studies of 5‐(5‐hydroxy‐3‐methyl‐1H‐pyrazol‐4‐yl)‐substituted 5H‐chromeno[2,3‐b]pyridines”, Journal of Heterocyclic Chem, 58:3 (2021), 793
M. N. Elinson, A. N. Vereshchagin, Yu. E. Ryzhkova, K. A. Karpenko, I. E. Ushakov, “Four component tandem Knoevenagel–Michael strategy for the assembly of arylaldehydes, N,N'-dimethylbarbituric acid, 4-hydroxy-6-methyl-2H-pyran-2-one and morpholine into unsymmetrical scaffold with three different heterocyclic rings”, Mendeleev Commun., 31:5 (2021), 698–700
Ankita Chaudhary, “Recent Advances in the Exploitation of Kojic Acid in Multicomponent Reactions”, COC, 24:14 (2020), 1643
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