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

doi:10.11944/j.issn.1000-0518.2017.03.160220

Chinese Journal of Applied Chemistry ›› 2017, Vol. 34 ›› Issue (3): 330-337.DOI: 10.11944/j.issn.1000-0518.2017.03.160220

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

DENG Youlin,TANG Shi(),YUAN Li,LI Zengzeng,WANG Liangneng,LI Liyang,HUANG Guixiu,LIU Yingying,WU Yiting,FU Li

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

Received:2016-05-26 Accepted:2016-09-21 Published:2017-02-27 Online:2017-02-27
Contact: TANG Shi
Supported by:
Supported by the National Natural Science Foundation of China(No.21462017), the Research Innovation Program for Graduates of Jishou University(No.JGY201636), the Research Program for Graduates of Science and technology department of Jishou University(No.15JDY001), the Hunan innovation base for the graduate student training(No.2014KFXM06)

Abstract

Abstract:

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.

Key words: isoquinolindione, benzamide, cascade cyclization, copper catalysis, alkyl azo compounds

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.

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

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