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Synthesis of homoisoflavonoids with a coumarin moiety and coumarin-pyrazole or coumarin-isoxazole hybrids based on them
(2022) Myshko, Nataliia; Mrug, Galyna; Bondarenko, Svetlana; Frasinyuk, Mihaylo
In this research in the oxa-Diels–Alder reaction of thermally generated ortho-quinone methides from 3-aryl-8-(N,N-dimethylaminomethyl)coumarines with (2E)-3-(N,N-dimethylamino)-1-(2-hydroxyphenyl)prop-2-en-1-ones and the subsequent cascade of reactions were obtained 8-[4-oxo-4H-chromen-3-yl)methyl]-7-hydroxy-3-phenyl-2H-chromen-2-ones. Synthesis of pyrazole-3-arylcoumarin hybrids was performed by recyclization of chromone core of homoisoflavonоids under hydrazine actions. Target isoxazoles were synthesized by the reaction of homoisoflavonоids with hydroxylamine hydrochloride in ethanol in presence of DBU
Reaction of ortho-Quinone Methides with Amphiphilic Nucleophiles
(2023) Myshko, Andrii; Mrug, Galyna; Myshko, Ivan; Bondarenko, Svetlana; Frasinyuk, Mihaylo
In continuing our studies on flavonoid-like scaffolds as privileged structures in medicinal chemistry, we studied the reaction of isoflavonoid derivatives with amphiphilic nucleophiles with heterocyclic cores. The direction of the reaction significantly depends on starting phenols, nucleophiles, and reaction conditions. Thus, applying phenolic Mannich bases led to formation of isoflavone-heterocycle hybrid via thermal formation of ortho-quinone methides in aprotic solvents and subsequent Michael addition