A Direct Synthesis of Substituted Exocyclic 1H‐pyrrol‐3(2H)‐ones by Base‐Mediated Multicomponent [3+2] Cycloaddition

Abstract

AbstractA one‐pot, three‐component, base‐mediated [3+2] cycloaddition reaction to synthesize 1H‐pyrrol‐3(2H)‐ones from readily available amino acid esters, aldehydes, and terminal alkynes was reported. Isolation of the intermediate and the detailed mechanistic study revealed the course of the reaction. This multi‐component reaction proceeds via imine formation followed by the nucleophilic addition of alkyne to form a propargylamine precursor. Base‐mediated conversion of propargylamine precursor into 1‐azadiene followed by in situ ketene formation leading to [3+2] cycloaddition that ultimately produces unusual 1H‐pyrrol‐3(2H)‐ones.