Trifluoroacetylation-Induced Houben−Hoesch-Type Cyclization of Cyanoacetanilides: Increased Nucleophilicity of CN Groups

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• 作者：Yusuke Kobayashi ; Kosuke Katagiri ; Isao Azumaya ; Takashi Harayama
• 刊名：Journal of Organic Chemistry
• 出版年：2010
• 出版时间：April 16, 2010
• 年：2010
• 卷：75
• 期：8
• 页码：2741-2744
• 全文大小：768K
• 年卷期：v.75,no.8(April 16, 2010)
• ISSN：1520-6904

文摘

Trifluoroacetic anhydride-mediated tandem trifluoroacetylation/cyclization of cyanoacetanilides proceeded efficiently under mild conditions to give 4-hydroxy-3-trifluoroacetylquinolin-2(1H)-ones in good yields. Isolation and direct observation of the reaction intermediates revealed that α-trifluoroacetylation resulted in the shortening of C≡N bonds and that the electron density of CN groups was high. A plausible reaction mechanism based on the results is also described.