L-Proline-Based Natural Deep Eutectic Solvents as Efficient Solvents and Catalysts for the Ultrasound-Assisted Synthesis of Aurones via Knoevenagel Condensation

Abstract

Aurones are minor flavonoids that possess a wide variety of bioactivity, including antioxidant, anticancer, and enzyme inhibitory activity. L-proline-based natural deep eutectic solvents (NaDES) were synthesized and applied as solvents and catalysts for the Knoevenagel condensation reaction between benzofuranone and substituted benzaldehydes to produce aurones in high yields and purity. The reaction between benzofuranone and vanillin served as the model reaction. After screening three NaDESs, and testing microwave, as well as ultrasound as energy sources, we concluded that the optimum results are obtained using L-proline/glycerol 1:2 as catalyst and solvent and ultrasound irradiation. The scope of the reaction was evaluated using a variety of benzaldehydes, and the corresponding aurones were obtained in moderate to satisfactory yields (57–89%) and high purity. An important additional feature of the described methodology is the recyclability and reusability of the NaDES, which was recycled and effectively reused after 6 cycles.

Keywords

• natural deep eutectic solvent
• ultrasound irradiation
• aurones
• Knoevenagel condensation