Zinc-Mediated Cyclodimerization of 1,5-Diaryl-1,4-pentadien-3-one in Aqueous Solution Under Ultrasound Irradiation

Abstract

Synthesis of 2-cinnamoyl-1-styryl-3,4-diarylcyclopentanol via cyclodimerization of 1,5-diaryl-1,4-pentadien-3-one mediated by zinc was carried out in good yields at room temperature in NH₄Cl (aq.) and tetrahydrofuran under ultrasonic irradiation. In comparison with conventional methods, the main advantages of the present procedure are shorter reaction time and better yields.

GRAPHICAL ABSTRACT

Keywords:

• 2-Cinnamoyl-1-styryl-3-4-diarylcyclopentanol
• cyclodimerization
• synthesis
• ultrasound irradiation

ACKNOWLEDGMENT

The Natural Science Foundation of Hebei Province (B2006000969), China, supported the project.

Notes

^a Substrate: 1,5-diphenyl-1,4-pentadien-3-one, 1 mmol; H₂O, 1 mL; THF, 4 mL; 30 °C; irradiation time, 0.5 h.

^a Stirring alone without ultrasound.