Copper-Catalyzed Aza-Michael Addition of Aromatic Amines or Aromatic Aza-Heterocycles to α,β-Unsaturated Olefins

A highly efficient and mild Cu-catalyzed conjugate addition reaction of aromatic amines and aromatic aza-heterocycles to α,β-unsaturated olefins is described. The transformation is promoted by 3–7 mol % of a Cu complex generated in situ from a mixture of inexpensive CuCl, a readily available phosphine or imidazolium salt, and KO<i>t</i>-Bu at ambient temperature. A wide range of β-amino sulfone, β-amino nitrile, and β-amino carbonyl compounds is efficiently and selectively synthesized in high yields (62–99%)

Copper-Catalyzed Aza-Michael Addition of 2‑Aminobenzoate to β‑Substituted α,β-Unsaturated Ketones: One-Pot Synthesis of 3‑Carbonyl-2-Substituted Quinolin-4(1<i>H</i>)‑ones

We present a new and straightforward one-pot process for the synthesis of 3-carbonyl-4-quinolone derivatives through highly efficient Cu-catalyzed aza-Michael addition of 2-aminobenzoates to β-substituted α,β-unsaturated ketones/cyclization/mild oxidation reactions. A broad range of new versatile 3-carbonyl-quinolin-4­(1<i>H</i>)-ones is prepared from readily available chemicals under mild reaction conditions with short reaction times, producing good to excellent yields (up to 99%)