One-Pot Wittig and Knoevenagel Reactions in Ionic Liquid as Convenient Methods for the Synthesis of Coumarin Derivatives

Abstract

Efficient synthesis of a variety of 3-substituted coumarins via NaOMe-catalyzed Knoevenagel condensation and one-pot preparation of 3,4-unsubstituted coumarins in the presence of NaOMe via Wittig reaction in room-temperature ionic liquids are described. Knoevenagel condensation of 2-hydroxybenzaldehyde with dimethyl- and diethylmalonate was performed with excellent yields in room-temperature ionic liquids. Although diethyl- and dimethylchloromalonates were mostly recovered unchanged in Knoevenagel condensation, higher conversions were observed via Wittig reaction of these compounds with 2-hydroxybenzaldehyde derivatives and triphenylphosphine. Other 2-hydroxybenzaldehyde derivatives, methyl- and ethylchloroacetates, were reacted in ionic liquids to afford simple coumarins in good yields. These reactions widen the applicability of ionic liquid in organic synthesis.

Keywords:

• Coumarins
• ionic liquid
• Knoevenagel reaction
• Wittig reaction

ACKNOWLEDGMENT

The office of the Research Vice Chancellor of Azerbaijan University of Tarbiat-Moallem is gratefully acknowledged.

Notes

^a Isolated yield after column chromatography.

^a Isolated yield after column chromatography.