Gao Hui, Yang Xiaobi, Tang Xinyu, Yin Pengcheng, Mao Zewei
College of Pharmaceutical Science, Yunnan University of Chinese Medicine, Kunming 650500, China.
Curr Org Synth. 2019;16(7):1032-1039. doi: 10.2174/1570179416666190723122816.
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.
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.
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.
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.
具有四个羰基官能团及其互变异构的酮 - 烯醇形式的2,2'-亚芳基双（3 - 羟基 - 5,5 - 二甲基 - 2 - 环己烯 - 1 - 酮）是一种重要的生物活性化合物，也是呫吨合成中的重要合成中间体。本研究旨在开发一种新的、简洁的合成2,2'-亚芳基双（3 - 羟基 - 5,5 - 二甲基 - 2 - 环己烯 - 1 - 酮）衍生物的方法。
发现TEAOH（20摩尔％）是通过Knoevenagel缩合/迈克尔加成串联反应制备2,2'-亚芳基双（3 - 羟基 - 5,5 - 二甲基 - 2 - 环己烯 - 1 - 酮）衍生物的简单而有效的催化剂。
开发了一种简洁实用的方法，用于在室温下于各种溶剂中由TEAOH催化一锅合成2,2'-亚芳基双（3 - 羟基 - 5,5 - 二甲基 - 2 - 环己烯 - 1 - 酮）衍生物。
该策略比传统合成方法具有多个优点，并且在室温下于各种溶剂中适用于多种芳香族和杂芳香族醛。
