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A Brief Synthesis of 2,2’-Arylmethylene Bis(3-hydroxy-5,5-dimethyl-2-cyclohexene-1- one) Catalyzed by TEAOH in Various Solvents

[ Vol. 16 , Issue. 7 ]

Author(s):

Hui Gao , Xiaobi Yang, Xinyu Tang, Pengcheng Yin and Zewei Mao*   Pages 1032 - 1039 ( 8 )

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.

Keywords:

Concise synthesis, TEAOH, cyclohexanedione, aromatic aldehyde, heteroaromatic aldehyde, traditional synthetic method.

Affiliation:

College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500, College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500, College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500, College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500, College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500

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