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ATOM-EFFICIENT SYNTHESIS OF HYBRID MOLECULES COMBINING FRAGMENTS OF TRIAZOLOPYRIMIDINES AND 3-ETHOXYCARBONYL-1-ETHYL-6-FLUOROQUINOLIN-4(1H)-ONE THROUGH 1,2,3-TRIAZOLE LINKER

Konstantin V. Savateev, Pavel A. Slepukhin, Svetlana K. Kotovskaya, Valery N. Charushin, Vladimir L. Rusinov, Oleg N. Chupakhin
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Abstract


An atom-efficient method toward hybrid molecules via azide-alkyne cycloaddition of 7-azido-3-ethoxycarbonyl-1-ethyl-6-fluoroquinolin-4(1H)-one and novel perspective triazolopyrimidines has been developed. This procedure features mild conditions and a broad substrate scope including hydrophobic and hydrophilic triazolopyrimidines. The synthesized hybrid structures combine fragments of fluoroquinolone with proved antibacterial activity and triazolopyrimidines, which may act as structural analogs of adenosine receptor effectors or antiviral azoloazine heterocycles.


Keywords


fluoroquinolones; nitro compounds; [1,2,4]triazolo[1,5-a]pyrimidines; azide-alkyne cycloaddition; chlorodeoxygenation; click chemistry; cyclization; hybrid molecules.

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