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

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• 作者：Davide Audisio ; Samir Messaoudi ; Jean-Franc抬ois Peyrat ; Jean-Daniel Brion ; Moua虃d Alami
• 刊名：Journal of Organic Chemistry
• 出版年：2011
• 出版时间：June 17, 2011
• 年：2011
• 卷：76
• 期：12
• 页码：4995-5005
• 全文大小：1048K
• 年卷期：v.76,no.12(June 17, 2011)
• ISSN：1520-6904

文摘

3-(N-Substituted) 4(1H)-quinolinones were synthesized using the copper-catalyzed Ullmann C鈥揘 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 K₂CO₃ 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.