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Lewis-Base-Catalyzed Alkylation Reaction of 4-Hydroxycoumarins with Allenoates: Regioselective Synthesis of 2H-[3,2-c] Furocoumarins and 4-Hydroxycoumarin Vinyl Ether Derivatives

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A milder, more regioselective and practical approach to C3 or O-alkylation reaction of 4-hydroxycoumarins has been established. Both 2H-[3,2-c] furocoumarins and 4-hydroxycoumarin vinyl ether derivatives could be efficiently prepared by… Click to show full abstract

A milder, more regioselective and practical approach to C3 or O-alkylation reaction of 4-hydroxycoumarins has been established. Both 2H-[3,2-c] furocoumarins and 4-hydroxycoumarin vinyl ether derivatives could be efficiently prepared by alkylating 4-hydroxycoumarins with electron-deficient allenoates catalyzed by PPh3 and DBU, respectively. The reaction outcomes can be controlled by changing the catalysts, starting with the same reaction substrates. Possible reaction mechanisms have also been proposed

Keywords: vinyl ether; furocoumarins hydroxycoumarin; reaction hydroxycoumarins; reaction; hydroxycoumarin vinyl; alkylation reaction

Journal Title: Asian Journal of Organic Chemistry
Year Published: 2017

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