Citation: DENG Youlin, TANG Shi, YUAN Li, LI Zengzeng, WANG Liangneng, LI Liyang, HUANG Guixiu, LIU Yingying, WU Yiting, FU Li. Copper-catalyzed Cyclization of Benamides and Alkyl Azo Compounds Leading to Isoquinolinediones Bearing α-Substituted Quaternary Carbon[J]. Chinese Journal of Applied Chemistry, ;2017, 34(3): 330-337. doi: 10.11944/j.issn.1000-0518.2017.03.160220 shu

Copper-catalyzed Cyclization of Benamides and Alkyl Azo Compounds Leading to Isoquinolinediones Bearing α-Substituted Quaternary Carbon

College of Chemistry and Chemical Engineering, Jishou University, Jishou, Hu'nan 416000, China

Corresponding author: TANG Shi, stang@jsu.edu.cn
Received Date: 26 May 2016
Revised Date: 21 July 2016
Accepted Date: 21 September 2016

Fund Project: Supported by the National Natural Science Foundation of China No.21462017the Hunan innovation base for the graduate student training No.2014KFXM06the Research Program for Graduates of Science and technology department of Jishou University No.15JDY001the Research Innovation Program for Graduates of Jishou University No.JGY201636

Figures(5)

A radical cyclization reaction of benzamides toward isoquinolinedione bearing α-substituted quaternary carbon was developed. Using alkyl azo compounds as tertiary radical sources, N-alkyl-N-methacryloylbenzamides underwent cascade radical addition/cyclization/C-C bond formation in the presence of Cu catalyst and air, and constructed triple-fold carbon-carbon bonds in a single step, leading to a series of isoquinolinediones in 41% to 71% yield. Notably, this work discovered a new type of radical precursor to α-functional tertiary radical and a protocol to incorporate two α-functional tertiary alkyl moieties. The broad substrate scope and high efficiency allow this method a cheap, simple and rapid catalytic synthetic entry to pharmaceutically interesting isoquinolindiones.
- isoquinolindione,
- benzamide,
- cascade cyclization,
- copper catalysis,
- alkyl azo compounds
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