Copper-Catalyzed [5+1] Annulation of 2-Ethynylanilines with an N,O-Acetal Leading to Construction of Quinoline Derivatives

被引：46

作者：

Sakai, Norio ^{[1
]}

Tamura, Kosuke ^{[1
]}

Shimamura, Kazuyori ^{[1
]}

Ikeda, Reiko ^{[1
]}

Konakahara, Takeo ^{[1
]}

机构：

[1] Tokyo Univ Sci RIKADAI, Dept Pure & Appl Chem, Fac Sci & Technol, Noda, Chiba 2788510, Japan

来源：

ORGANIC LETTERS | 2012年 / 14卷 / 03期

关键词：

O-ALKYNYLARYL ISOCYANIDES; ONE-POT SYNTHESIS; FRIEDLANDER SYNTHESIS; INTRAMOLECULAR CYCLIZATION; 2-SUBSTITUTED QUINOLINES; MOLECULAR-IODINE; TANDEM SYNTHESIS; PRIMARY AMINES; INDOLES; SKRAUP;

D O I：

10.1021/ol203360g

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel copper-catalyzed [5 + 1] annulation of 2-ethynylanilines with an N,O-acetal, which functioned as a Cl part, leading to the preparation of quinoline derivatives with an ester substituent on the 2-position is described. A combination of CuBr2 and trifluoroacetic acid (TFA) promoting [5 + 1] annulation of the 2-ethynylaniline with ethyl glyoxylate is also demonstrated.

引用

页码：836 / 839

页数：4

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