Copper-Catalyzed Three-Component Synthesis of 2-Iminodihydrocoumarins and 2-Iminocoumarins

被引：51

作者：

Shen, Yang ^{[1
]}

Cui, Sunliang ^{[1
]}

Wang, Jing ^{[1
]}

Chen, Xiaopeng ^{[1
]}

Lu, Ping ^{[1
]}

Wang, Yanguang ^{[1
,2
]}

机构：

[1] Zhejiang Univ, Dept Chem, Hangzhou 310027, Zhejiang, Peoples R China

[2] Lanzhou Univ, State Key Lab Appl Organ Chem, Lanzhou 730000, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2010年 / 352卷 / 07期

基金：

中国国家自然科学基金;

关键词：

cascade reactions; copper; coumarins; ketenimines; multicomponent reactions; ONE-POT SYNTHESIS; FLUORESCENT CA2+ INDICATORS; MULTICOMPONENT REACTION; SULFONYL AZIDES; FACILE ACCESS; ENANTIOENRICHED PIPERIDINES; EFFICIENT SYNTHESIS; CASCADE REACTIONS; AMIDE SYNTHESIS; WATER;

D O I：

10.1002/adsc.200900890

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

An efficient synthesis of N-sulfonyl-substituted 2-imino-3,4-dihydrocoumarins and 2-iminocoumarins via a copper-catalyzed multicomponent reaction of sulfonyl azides with terminal alkynes and beta-(ortho-hydroxypheny1)-alpha,beta-unsaturated ketones or ortho-hydroxyphenylpropiolates has been developed. The cascade process involves trapping the keteimine by a nucleophilic addition and an intramolecular Michael addition. This methodology could well be extended to the concise synthesis of the polysubstituted piperidine scaffold.

引用

页码：1139 / 1144

页数：6

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