Synthesis of 2-alkyl-substituted isoflavonoid analogues with non-aromatic ring A on the basis of 2-[2-(aryl)acetyl]cyclohexane-1,3-diones and carboxylic acid anhydrides
https://doi.org/10.29235/1561-8323-2025-69-1-32-39
Abstract
A simple and convenient method for the synthesis of 2-alkyl-substituted analogues of isoflavonoids with nonaromatic ring A is proposed. The method consists of acylation of 2-[2-(aryl)acetyl]cyclohexane-1,3-diones with carboxylic acid anhydrides followed by intramolecular aldol-crotonic condensation of the resulting enolacylates in the presence of basic agents (triethylamine, sodium acetate, potassium carbonate). 2-[2-(Aryl)acetyl]cyclohexane-1,3-diones were obtained by condensation of 5-substituted cyclohexane-1,3-diones with arylacetic acids under the action of dicyclohexylcarbodiimide and 4-(dimethylamino)pyridine-catalyzed O-C isomerization of the resulting O-acylates.
About the Authors
F. S. Pashkovsky
Institute of Bioorganic Che mistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Pashkovsky Felix S. – Ph. D. (Chemistry), Leading Researcher
5/2, Kuprevich Str., 220141, Minsk
D. B. Rubinov
Institute of Bioorganic Che mistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Rubinov Dmitry B. – Ph. D. (Chemistry), Leading Researcher
5/2, Kuprevich Str., 220141, Minsk
V. I. Linnik
Institute of Bioorganic Che mistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Linnik Vladislav I. – Master of Science, Junior Researcher
5/2, Kuprevich Str., 220141, Minsk
F. A. Lakhvich
Institute of Bioorganic Che mistry of the National Academy of Sciences of Belarus
Belarus
Belarus
Lakhvich Fedor A. – Academician, D. Sc. (Chemistry), Professor, Chief Researcher
5/2, Kuprevich Str., 220141, Minsk
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