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
收藏
页码：5914 / 5918
页数：5
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