Synthesis of 7-tert-Alkylated Isoquinolinedione via Copper-catalyzed Aerobic Cyclization of Benzamides

doi:10.11944/j.issn.1000-0518.2016.10.160127

Chinese Journal of Applied Chemistry ›› 2016, Vol. 33 ›› Issue (10): 1175-1181.DOI: 10.11944/j.issn.1000-0518.2016.10.160127

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Synthesis of 7-tert-Alkylated Isoquinolinedione via Copper-catalyzed Aerobic Cyclization of Benzamides

DENG Youlin,TANG Shi(),LI Liyang,FU Meiling,WANG Liangneng,CHEN Lanyan,ZHOU Shangrui

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

Received:2016-03-28 Accepted:2016-06-20 Published:2016-10-08 Online:2016-10-08
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 Hu'nan Innovation Base for the Graduate Student Training(No.2014KFXM06)

Abstract

Abstract:

A cheap and simple radical cyclization reaction of benzamides toward 7-tert-alkylated isoquinolinedione was developed. In the presence of cheap CuI and air, various N-alkyl-N-methacryloyl benzamides with azodiisobutyronitrile underwent cascade radical addition/cyclization/C-C coupling reactions, leading to a series of biologically active isoquinolinediones in the yields of 73% to 52%. This study provides a rapid, simple and mild entry to the synthesis of pharmaceutically interesting isoquinolindiones.

Key words: tert-alkylated isoquinolindione, benzamide, aerobic cyclization, copper catalysis

DENG Youlin, TANG Shi, LI Liyang, FU Meiling, WANG Liangneng, CHEN Lanyan, ZHOU Shangrui. Synthesis of 7-tert-Alkylated Isoquinolinedione via Copper-catalyzed Aerobic Cyclization of Benzamides[J]. Chinese Journal of Applied Chemistry, 2016, 33(10): 1175-1181.

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Synthesis of 7-tert-Alkylated Isoquinolinedione via Copper-catalyzed Aerobic Cyclization of Benzamides

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