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A General Copper Powder-Catalyzed Ullmann-Type Reaction of 3-Halo-4(1 H )-quinolones With Various Nitrogen-Containing Nucleophiles

2011; American Chemical Society; Volume: 76; Issue: 12 Linguagem: Inglês

10.1021/jo200680j

1520-6904

Davide Audisio, Samir Messaoudi, Jean‐François Peyrat, Jean‐Daniel Brion, Mouâd Alami,

Synthesis and Biological Evaluation

3-(N-Substituted) 4(1H)-quinolinones were synthesized using the copper-catalyzed Ullmann C-N bond forming strategy in moderate to quantitative yields. Starting from 3-halo-4(1H)-quinolones, various nucleophiles including amides, lactams, sulfonamides and NH-containing azoles have been used successfully. In all cases, the reactions take place rapidly in toluene and proceed by using copper powder as a catalyst, DMEDA as a ligand and K(2)CO(3) as a base. In addition, other related heterocycles such as 3-bromoquinolin-2(1H)-ones, 3-bromocoumarin, and 3,5-dibromo-2-pyridone show good to very high reactivity with various nucleophiles under our Cu/DMEDA catalyst system.