An easy approach to dihydrochalcones via chalcone in situ hydrogenation

Abstract

Dihydrochalcones are polyphenols that exhibit a diversity of bioactivities, namely anti-inflammatory, antimicrobial and antiviral. We have explored the synthetic access to such molecular entities, and describe now an easy and scalable approach based on reduction of the olefinic double bond of chalcone precursors via in situ hydrogenation with the system Et3SiH-Pd/C in very high yield. The intermediate chalcones were synthesized also by a simple and efficient microwave-assisted Claisen-Schmidt condensation of aromatic aldehydes with acetophenones, conveniently protected with ethoxymethyl ether, if required. Chalcones were obtained as single reaction product in high yield in 2-3 h, while under conventional conditions at room temperature the reaction was carried out with completion only after 24 h. In addition, microwave irradiation has proven very efficient for deprotection of ethoxymethyl ether with iron chloride in only 10 min and very high yield.