铜催化苯甲酰胺有氧环化合成7-叔烷基异喹啉二酮

doi:10.11944/j.issn.1000-0518.2016.10.160127

摘要/Abstract

摘要：

发展了一种高效、简单的铜/空气催化体系催化的苯甲酰胺串联自由基环化合成7-叔烷基异喹啉二酮的反应。在廉价CuI存在下,空气环境中,N-烷基-N-甲基丙烯酰基苯甲酰胺与AIBN发生串联自由基加成/环化/碳碳偶联反应,以52%~73%的产率合成了一系列的7-取代异喹啉二酮。此研究为合成具有潜在药用价值的含氰取代异喹啉二酮提供了一条快速、简单、温和的构建途径。

关键词: 叔烷基异喹啉二酮, 苯甲酰胺, 有氧环化, 铜催化

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

邓佑林, 唐石, 李立洋, 付美玲, 王良能, 陈蓝艳, 周上睿. 铜催化苯甲酰胺有氧环化合成7-叔烷基异喹啉二酮[J]. 应用化学, 2016, 33(10): 1175-1181.

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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