An expedient method for regioselective methylation of catechol coumarins

Abstract

An expedient and efficient method for selective methylation of catechol coumarins by working with different alkalis under appropriate reaction conditions is reported. Esculetins were selectively methylated at position 6 and position 7 in good yield using CH₃I in the presence of NaH and Na₂CO₃, respectively. However, daphnetins showed less regioselectivity under the same reaction conditions. Furthermore, the site preference for the methylation reaction was interpreted by the density functional theory at B3LYP/6-31+G(d) level.

Keywords

Catechol coumarin / Regioselective methylation / Density functional theory

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