Novel and Convenient Synthesis of Substituted Quinolines by Copper- or Palladium-Catalyzed Cyclodehydration of 1-(2-Aminoaryl)-2-yn-1-ols

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• 作者：Bartolo Gabriele ; Raffaella Mancuso ; Giuseppe Salerno ; Giuseppe Ruffolo ; Pierluigi Plastina
• 刊名：Journal of Organic Chemistry
• 出版年：2007
• 出版时间：August 31, 2007
• 年：2007
• 卷：72
• 期：18
• 页码：6873 - 6877
• 全文大小：112K
• 年卷期：v.72,no.18(August 31, 2007)
• ISSN：1520-6904

文摘

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A general and convenient synthesis of substituted quinolines by regioselective copper- or palladium-catalyzed 6-endo-dig cyclization-dehydration of 1-(2-aminoaryl)-2-yn-1-ols is reported. The crudesubstrates were easily obtained by the Grignard reaction between the appropriate alkynylmagnesiumbromide and 2-aminoaryl ketones and could be used without further purification for the subsequentcyclization step. Heteroannulation reactions were carried out in MeOH or DME as the solvent at 60 or100 C in the presence of CuCl₂ or PdX₂ (in conjunction with 10 equiv of KX, X = Cl, I) as the catalystto afford the quinoline derivatives in good to excellent isolated yields based on starting 1-(2-aminoaryl)-2-yn-1-ols (66-90%).