Construction of Isoquinolin-1(2H)-ones by Copper-Catalyzed Tandem Reactions of 2-(1-Alkynyl)benzaldimines with Water

被引：26

作者：

Zhang, Mingliang ^{[1
]}

Zhang, Hui-Jun ^{[1
]}

Ruan, Wenqing ^{[1
]}

Wen, Ting-Bin ^{[1
]}

机构：

[1] Xiamen Univ, Coll Chem & Chem Engn, Dept Chem, Xiamen 361005, Fujian, Peoples R China

来源：

EUROPEAN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 2015卷 / 27期

基金：

中国国家自然科学基金;

关键词：

Homogeneous catalysis; Copper; Cyclization; Oxidation; Tandem reaction; Nitrogen heterocycles; ONE-POT SYNTHESIS; EFFICIENT SYNTHESIS; CONCISE SYNTHESIS; SUBSTITUTED; 3-METHYLENEISOINDOLIN-1-ONES; 3,4-DISUBSTITUTED ISOQUINOLINES; INTRAMOLECULAR CYCLIZATION; ELECTROPHILIC CYCLIZATION; STEREOSELECTIVE-SYNTHESIS; NUCLEOPHILIC-ADDITION; BIOLOGICAL EVALUATION;

D O I：

10.1002/ejoc.201500908

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

The Cu(OAc)(2)-catalyzed tandem reaction of 2-(1-alkynyl)-benzaldimines with water for the synthesis of isoquinolin1-(2H)-ones was developed. Moreover, 4-halogen-substituted isoquinolin-1(2H)-ones were obtained in good yields simply by including N-halosuccinimides (NXS: X = Cl, Br, I) in the reaction system. Mechanistic studies indicated that the reactions are probably initiated by highly regioselective intramolecular cyclization of 2-(1-alkynyl) benzaldimines to give the corresponding isoquinolinium intermediates.

引用

页码：5914 / 5918

页数：5

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