Title:A Brief Synthesis of 2,2’-Arylmethylene Bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1- one) Catalyzed by TEAOH in Various Solvents
Volume: 16
Issue: 7
Author(s): Hui Gao , Xiaobi Yang, Xinyu Tang, Pengcheng Yin and Zewei Mao*
Affiliation:
- College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500,China
Keywords:
Concise synthesis, TEAOH, cyclohexanedione, aromatic aldehyde, heteroaromatic aldehyde, traditional synthetic method.
Abstract:
Aims and Objectives: 2,2’-Arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) having
four carbonyl functionalities along with their tautomeric keto-enol forms, is an important biologically active
compound and important synthetic intermediate in the synthesis of xanthenes. This study was conducted in
order to develop a new and concise method of synthesis of 2,2’-arylmethylene bis (3-hydroxy-5,5-dimethyl-2-
cyclohexene-1-one) derivatives.
Materials and Methods: TEAOH (20 mol %) was fond to be as a simple and efficient catalyst for the
preparation of 2,2’-arylmethylene bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives by the
Knoevenagel condensation/Michael addition tandem reactions.
Results: A concise and practical method was developed for one-pot synthesis of 2,2’-arylmethylene bis(3-
hydroxy-5,5-dimethyl-2-cyclohexene-1-one) derivatives catalyzed by TEAOH at room temperature in various
solvents.
Conclusion: This strategy provides several advantages over the traditional synthetic method, and is applicable
to a wide variety of aromatic and heteroaromatic aldehydes at room temperature in various solvents.