Three-Component Cascade Synthesis of Carbazoles through [1s,6s] Sigmatropic Shift under Metal-Free Conditions

被引：22

作者：

Chen, Shanping ^{[1
]}

Jiang, Pingyu ^{[1
]}

Wang, Pu ^{[1
]}

Pei, Yong ^{[1
]}

Huang, Huawen ^{[1
]}

Xiao, Fuhong ^{[1
]}

Deng, Guo-Jun ^{[1
]}

机构：

[1] Xiangtan Univ, Key Lab Green Organ Synth & Applicat Hunan Prov, Key Lab Environm Friendly Chem & Applicat, Minist Educ,Coll Chem, Xiangtan 411105, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2019年 / 84卷 / 06期

基金：

中国国家自然科学基金;

关键词：

C-H FUNCTIONALIZATION; ONE-POT SYNTHESIS; EFFICIENT CONSTRUCTION; SUBSTITUTED CARBAZOLES; CLAUSINE-L; INDOLES; ANNULATION; ALKALOIDS; ACID; CYCLIZATION;

D O I：

10.1021/acs.joc.8b02994

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A novel method was developed for the synthesis of substituted carbazoles from commercially available starting materials under metal-free conditions. This strategy involves a [1s,6s] sigmatropic shift step and introduces an electron-withdrawing ester substituent at the C2 position of the carbazole ring. The present protocol afforded the desired carbazole derivatives with good regioselectivity and well functional group tolerance. DFT calculations were carried out to support the reaction pathway.

引用

收藏

页码：3121 / 3131

页数：11

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