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ELECTROCATALYTIC TANDEM ASSEMBLY OF ALDEHYDES WITH 2-THIOBARBITURIC ACID INTO 5,5'-(ARYLMETHYLENE)BIS(1,3-DIETHYL-2-THIOBARBITURIC ACIDS) AND EVALUATION OF THEIR INTERACTION WITH CATALASES

Michail N. Elinson, Anatoly N. Vereshchagin, Yuliya E. Ryzhkova, Kirill A. Karpenko, Fedor V. Ryzhkov, Mikhail P. Egorov
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Abstract


Electrocatalytic transformation of aldehydes with two equivalents of 1,3-diethyl-2-thiobarbituric acid has been carried out in alcohols in an undivided cell in the presence of sodium halides with the selective formation of the substituted 5,5' -(arylmethylene)bis(1,3-diethyl-2-thiobarbituric acids) in 87–98% yields and with 870–980% current efficiency. This new one-pot electrochemically induced tandem Knoevenagel–Michael process is a simple and efficient approach to substituted 5,5'-(arylmethylene)bis(1,3-diethyl-2-thiobarbituric acids) containing two 1,3-diethyl-2-thiobarbituric acid fragments separated by C-aryl-substituted spacer, which are promising compounds for different biomedical applications, including anticonvulsant, antiAIDS agents and anti-inflammatory remedies. Theoretical studies were carried out to investigate the interaction of the synthesized compounds with beef and human catalases.

Keywords


aldehydes; 5,5'-(arylmethylene)bis(1,3-diethyl-2-thiobarbituric acids); 1,3-diethyl-2-thiobarbituric acid; docking studies; electrocatalysis; electroorganic chemistry.

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