Synthesis of biscoumarins using recyclable and biodegradable task-specific ionic liquids

Α. Tzani, A. Douka, A. Papadopoulos, E.A. Pavlatou, E. Voutsas, A. Detsi

ACS Sustainable Chemistry and Engineering (2013), 1 (9), 1180-1185

In the frame of research that examines the use of task-specific ionic liquids (ILs) for developing green methodologies toward novel bioactive compounds, ethanolamine-derived ILs were synthesized and used as solvents and catalysts in a domino Knoevenagel–Michael reaction. After extended optimization studies regarding the most important reaction parameters such as reaction time, temperature, and molar ratio of reactants, it was ascertained that the reaction between 4-hydroxy-coumarin and various benzaldehydes in the synthesized ILs proceeded smoothly at 40°C in 3h, providing the desired biscoumarins in very satisfactory yields (up to 97%) and high purity after simple workup. The task-specific ILs were recycled and reused three times without a noticeable decrease in their catalytic activity. Moreover, the biodegradability potential of the synthesized ILs has been investigated by applying the biological oxygen demand (BOD-5) closed bottle test. The results indicated that organic carbon was biodegraded up to 59% within five days.

doi: 10.1021/sc4001093

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