Copper(II)-Catalyzed Sequential C,N-Difunctionalization of 1,4-Naphthoquinone for the Synthesis of Benzo[f]indole-4,9-diones under Base-Free Condition

被引：34

作者：

Sun, Jin-Wei ^{[1
]}

Wang, Xiang-Shan ^{[1
]}

Liu, Yun ^{[1
]}

机构：

[1] Jiangsu Normal Univ, Sch Chem & Chem Engn, Xuzhou 221116, Jiangsu, Peoples R China

来源：

JOURNAL OF ORGANIC CHEMISTRY | 2013年 / 78卷 / 20期

基金：

中国国家自然科学基金;

关键词：

FREE-RADICAL REACTIONS; PHOTOINDUCED MOLECULAR-TRANSFORMATIONS; REGIOSELECTIVE PHOTOADDITION; 2-AMINO-1,4-NAPHTHOQUINONES; DERIVATIVES; 1H-BENZ<F>INDOLE-4,9-DIONES; FUNCTIONALIZATION; AZIDOQUINONES; KINAMYCINS; ANALOG;

D O I：

10.1021/jo401842d

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

An efficient synthesis of benzo[f]indole-4,9-diones has been achieved by copper(II)-catalyzed naphthoquinone sequential C,N-difunctionalization reactions with beta-enaminones. New C-C and C-N bonds are easily formed in the reaction course. Copper(II) salt plays a dual role as Lewis acid and oxidative catalyst, and O-2 acts as the terminal oxidant. The advantage of this reaction is the high atom economy with broad substrate scope and excellent yields. The reaction can be scaled up to using at least grams of substrates.

引用

页码：10560 / 10566

页数：7