Efficient Synthesis of Ferrocenylcyclohexenone Under Solvent-Free Conditions

Abstract

An efficient method for the synthesis of a series of ferrocenylcyclohexenones via tandem Michael–aldol reaction of ferrocenyl-substituted chalcones with dibenzyl ketone under solvent-free conditions is described. It was found that the factors including the electronic nature of chalcone, basicity of the base, reaction time, and temperature have effects on the formation of the ferrocenylcyclohexenones.

Keywords:

• Chalcone
• crystal structure
• cyclohexenone
• ferrocene
• solvent-free

ACKNOWLEDGMENTS

This work was partially supported by the National Natural Science Foundation of China (No. 20672079), Natural Science Foundation of Jiangsu Province (No. BK2006048), Nature Science of Jiangsu Province for Higher Education (No. 05KJB150116), Nature Science Key Basic Research of Jiangsu Province for Higher Education (No. 06KJA15007), Specialized Research Fund for the Doctoral Program of Higher Education (No. 20060285001), Key Laboratory of Organic Synthesis of Jiangsu Province (No. JSK008), and Key Project in Science and Technology Innovation Cultivation Program of Suzhou University.

Notes

^a The authenticity of product was characterized by its IR, ¹H NMR, and HRMS analyses.

^b Isolated yields.

^a Isolated yields after silica-gel column chromatography.

^b The reaction was incomplete after reacting for 1 h, and the existence of substrate was observed by TLC analysis.

^a The authenticity of product was characterized by its IR, ¹H NMR, and HRMS analyses.

^b Isolated yields.