Sc(OTf)3-promoted formal insertion of 4-diazo-1,4-dihydroisoquinoli-n-3-ones into C-H bond of 1,3-dicarbonyl compounds: Synthesis of 2-(3-oxo-1,2,3,4-tetrahydroisoquinolin-4-yl)-1,3-diarylpropane-1,3-diones

被引：1

作者：

Xie, Jianwei ^{[1
]}

Suleman, Muhammad ^{[1
]}

Qian, Guxin ^{[1
]}

Lu, Ping ^{[1
]}

Wang, Yanguang ^{[1
]}

机构：

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

来源：

TETRAHEDRON | 2023年 / 143卷

基金：

中国国家自然科学基金;

关键词：

Diazo compounds; Lewis acid catalysis; Heterocycles; CHEMOSELECTIVE CARBENE INSERTION; DIAZO-COMPOUNDS; ENANTIOSELECTIVE SYNTHESIS; 3-COMPONENT REACTION; ALPHA-DIAZOESTERS; DIAZOCARBONYL; FUNCTIONALIZATION; REARRANGEMENT; HETEROCYCLES; RHODIUM(II);

D O I：

10.1016/j.tet.2023.133558

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A facile and efficient synthesis of novel 2-(1,2,3,4-tetrahydroisoquinolin-4-yl)-1,3-diarylpropane-1,3-diones via the Sc(OTf)3-promoted reaction between 4-diazo-1,4-dihydroisoquinolin-3-ones and 1,3-dicarbonyl compounds is reported. This formal C-H bond insertion involves an activation of 1,3-dicarbonyl compounds with generation of triflic acid by-product, a formation of diazonium intermediate from diazo component by triflic acid promotion, and a subsequent intermolecular nucleophilic substitution step. Readily available starting materials, cheap catalyst, broad substrate scope (22 examples, up to 92% yield), and mild reaction conditions are the merits of this reaction.

引用

页数：9

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