Multicomponent synthesis of new barbituric acid derivatives

A new type of the four-component tandem Knoevenagel—Michael reaction was discovered, which used arylaldehydes, N,N ′-dimethylbarbituric acid, dimedone, and morpholine or piperidine in organic solvents or in water. The reaction proceeded under mild conditions at room temperature with the formation of...

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Bibliographic Details
Published in:Russian chemical bulletin 2024-05, Vol.73 (5), p.1286-1296
Main Authors: Elinson, M. N., Vereshchagin, A. N., Ryzhkova, Yu. E., Karpenko, K. A., Iliyasov, T. M., Kalashnikova, V. M., Egorov, M. P.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Chemistry/Food Science
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Inorganic Chemistry
Michael reaction
Organic Chemistry
Piperidine
Reaction products
Room temperature
Substitutes
X-ray diffraction
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Summary:A new type of the four-component tandem Knoevenagel—Michael reaction was discovered, which used arylaldehydes, N,N ′-dimethylbarbituric acid, dimedone, and morpholine or piperidine in organic solvents or in water. The reaction proceeded under mild conditions at room temperature with the formation of a new substituted unsymmetrical polycyclic ionic scaffold in 83–98% yields. The structures of the reaction products were confirmed by X-ray diffraction analysis on the example of two compounds. The further oxidative cyclization of the Knoevenagel—Michael reaction products led to unsymmetrical substituted dihydrofurans spiro-annulated with N,N ′-dimethylbarbituric acid. The structures of the synthesized compounds were confirmed by X-ray diffraction analysis.
ISSN:1066-5285
1573-9171
DOI:10.1007/s11172-024-4245-3