Ag‐Catalyzed Trifluoromethylative Ring Expansion of Isatins and Isatin Ketimines with Trifluorodiazoethane

Abstract

A general method for the construction of trifluoromethylated 2-quinolinones has been established herein by using a trifluoromethylative ring expansion of isatin with trifluorodiazoethane. The strategy provides a platform for the rapid synthesis of a wide range of substituted 3-hydroxy-4-trifluoromethyl-2-quinolinones. This operationally simple and robust Ag-catalyzed protocol successfully transforms isatin ketimines to 3-amino-4-trifluoromethylquinolinones in excellent yields. The utility of this novel method is further illustrated by the conversion of the products into various synthetically and medicinally relevant molecules.

Topics & Concepts