Fast and efficient synthesis of flavanones from cinnamic acids

ABSTRACT

A fast and efficient synthesis of flavanones from cinnamic acids in three steps has been developed. First, the cinnamic acid was converted to cinnamyol chlorides using SOCl₂. The acid chlorides were then treated with substituted phenols in BF₃ · OEt₂ to furnish corresponding chalcones in 42(75% yields. Base-catalyzed cyclization of the chalcones at room temperature afforded corresponding flavones in 85–95% yields. The conversion of the cinnamic acid derivatives to corresponding chalcones was found to be sensitive to the position and nature of the substituents on the aromatic rings.

GRAPHICAL ABSTRACT

KEYWORDS:

• Acylation
• chalcone
• cinnamic acid
• flavanone

Acknowledgment

We thank Mr S. M. Marape (University of Botswana) for NMR experiments.