Access to 2-pyridinones comprising enaminonitriles via AgOAc promoted cascade reactions of thioesters with aminomethylene malononitriles

Abstract

The facile synthesis of 2-pyridinones containing enaminonitriles from thioesters with aminomethylene malononitriles is achieved through an AgOAc-promoted acylation/cyclization/tautomerization cascade reaction. Control experiments reveal that AgOAc acts as a versatile promoter, activating both thioester and cyano groups while also serving as a Brønsted base in the cascade sequence. Moreover, 2-pyridinones were transformed into biologically significant 2-pyridinone-fused 2-pyrimidones with intriguing fluorescence emission properties.