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

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

doi:10.1016/j.ultsonch.2014.05.010

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

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

Authors

Ya-Li Song¹, Yun-Fang Dong², Fan Wu², Tao Yang², Geng-Liang Yang³

Affiliations

¹ 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. Electronic address: yalisong@hbu.edu.cn.
² 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.
³ 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. Electronic address: ygl@hbu.edu.cn.

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

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.

Keywords: 3-Hydroxy-5,5-dimethyl-2-[phenyl(phenylthio)methyl]cyclohex-2-enone; 5,5-Dimethyl-1,3-cyclohexanedione; DBSA; Three-component reaction; Ultrasound.

Publication types

Research Support, Non-U.S. Gov't