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

被引：14

作者：

Kobayashi, Yusuke ^{[1
]}

Katagiri, Kosuke ^{[1
]}

Azumaya, Isao ^{[1
]}

Harayama, Takashi ^{[1
]}

机构：

[1] Tokushima Bunri Univ, Fac Pharmaceut Sci, Kagawa 7692193, Japan

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2010年 / 75卷 / 08期

基金：

日本学术振兴会;

关键词：

FRIEDEL-CRAFTS ACYLATION; ARYL KETONES; NITRILES; ALKALOIDS; ANHYDRIDE; QUINOLINE; AMINES;

D O I：

10.1021/jo100220m

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

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 alpha-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.

引用

页码：2741 / 2744

页数：4

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