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超声作用下单锅三组分合成3-羟基-5,5-二甲基-2-[苯基(苯硫基)甲基]环己-2-烯酮衍生物

One-pot three-component synthesis of 3-hydroxy-5,5-dimethyl-2-[phenyl(phenylthio)methyl]cyclohex-2-enone derivatives under ultrasound.

作者信息

Song Ya-Li, Dong Yun-Fang, Wu Fan, Yang Tao, Yang Geng-Liang

机构信息

Key Laboratory for Pharmaceutical Quality Control of Hebei Province, Key Laboratory of Medical Chemistry and Molecular Diagnosis, Ministry of Education, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002, China.

Key Laboratory for Pharmaceutical Quality Control of Hebei Province, Key Laboratory of Medical Chemistry and Molecular Diagnosis, Ministry of Education, College of Pharmaceutical Sciences, Hebei University, Baoding, Hebei, 071002, China.

出版信息

Ultrason Sonochem. 2015 Jan;22:119-24. doi: 10.1016/j.ultsonch.2014.05.010. Epub 2014 Jun 2.

DOI:10.1016/j.ultsonch.2014.05.010
PMID:24998092
Abstract

3-Hydroxy-5,5-dimethyl-2-[phenyl(phenylthio)methyl]cyclohex-2-enone is synthesized via one-pot three-component reactions of aromatic aldehyde, substituted thiophenol and 5,5-dimethyl-1,3-cyclohexanedione catalyzed by p-dodecylbenzene sulfonic acid (DBSA) under ultrasound. Under ultrasound irradiation the yields are much higher (sometimes substantially, by almost double) and the reaction time decreases substantially, the reaction conditions are milder. This method provides several advantages such as environment friendliness, high yields and simple work-up procedure and the protocol provides a novel alternative for the synthesis of thioether.

摘要

3-羟基-5,5-二甲基-2-[苯基(苯硫基)甲基]环己-2-烯酮是通过对十二烷基苯磺酸(DBSA)在超声作用下催化芳香醛、取代苯硫酚和5,5-二甲基-1,3-环己二酮的一锅三组分反应合成的。在超声辐射下,产率要高得多(有时大幅提高,几乎翻倍),反应时间大幅缩短,反应条件更温和。该方法具有环境友好、产率高和后处理程序简单等优点,该方案为硫醚的合成提供了一种新的替代方法。

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