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Current Organic Synthesis


ISSN (Print): 1570-1794
ISSN (Online): 1875-6271

Research Article

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

Author(s): Hui Gao , Xiaobi Yang, Xinyu Tang, Pengcheng Yin and Zewei Mao*

Volume 16 , Issue 7 , 2019

Page: [1032 - 1039] Pages: 8

DOI: 10.2174/1570179416666190723122816

Price: $65


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.

Graphical Abstract
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