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■ Silver-Catalyzed Conversion of CO2 and 2-Ethynylanilines into 4-Hydroxyquinolin-2(1H)-ones in Protic Ionic Liquid at Atmospheric Pressure

Qi Feng,* Keyan Yuan, Miaoqing Zhu, Jingzon You, and Congmin Wang

*Department of Science Education, Zhejiang International Studies University, No. 299, Liuhe Road, Zhejiang International Studies University, Hangzhou, Zhejiang, China

Abstract

4-Hydroxyquinolin-2(1H)-ones are core structural subunits frequently found in many pharmacological compounds and the synthesis of this kind of compounds is highly desirable. An efficient protic ionic liquid and AgNO3 catalytic system was developed for the preparation of various 4-hydroquinolin-2(1H)-ones from CO2 and 2-ethynylanilines in moderate to excellent yields (65-94%). It was found that [HTMG][Im], a simple and easily prepared protic ionic liquid comprising a 1,1,3,3-tetramethylguanidinium cation and a imidazolide anion, could act as both the solvent and reaction promoter, and that the reaction could be efficient carried out with a mount of 2 mol% AgNO3 under atmospheric pressure of CO2 at 60 ℃. This method provides a new approach for the synthesis of 4-hydroxyquinolin-2(1H)-ones.