An Exploration of Organocatalyst 1,4-Diazabicyclo[2.2.2]octane in the Direct Regioselective and Chemoselective γ-Addition of β-Keto Amide on Isatin to Afford Structurally Diverse Molecular Frameworks

Abstract

An efficient protocol promoted by 1,4‐diazabicyclo[2.2.2]octane is described for the regioselective and chemoselective γ-addition of β-keto amides on isatins to afford γ-(3-hydroxy-2-oxindole)-β-keto amide structural framework under metal-free conditions. The developed method is mild, generates high yields, and is applicable for a variety of isatin electrophiles as well as β-keto amides. Moreover, the procedure is very handy and environmentally benign in nature, and provides direct access for the synthesis of diverse functionalized 3-β-keto amide-substituted 3-hydroxy-2-oxindole structural scaffolds from readily available starting materials.