Transition-Metal-Free Aminoacylation of Ynones with Amides: Synthesis of 3‑Carbonyl-4-quinolinones or Functionalized Enaminones

A transition-metal-free tandem process for the synthesis of substituted quinolin-4­(1<i>H</i>)-ones or enaminones is presented. A base-promoted insertion of ynones into the C–N σ-bond of amides is the key step in this process, which provides the corresponding aminoacylation products in good to high yields. Quinolin-4­(1<i>H</i>)-ones are selectively formed via the subsequent N-cyclization pathway in the cases of ynones bearing an <i>ortho</i>-bromo-substituted aryl ring. Easily accessible starting materials and high atom economy make this procedure attractive