Tunable Synthesis of 3-Hydroxylisoquinolin-1,4-dione and Isoquinolin-1-one Enabled by Copper-Catalyzed Radical 6-endo Aza-cyclization of 2-Alkynylbenzamide
Tunable Synthesis of 3-Hydroxylisoquinolin-1,4-dione and Isoquinolin-1-one Enabled by Copper-Catalyzed Radical 6-endo Aza-cyclization of 2-Alkynylbenzamide
复制标题
铜催化2-炔基苯甲酰胺自由基6-内氮杂环化可调节合成3-羟基异喹啉-1,4-二酮和异喹啉-1-酮
DOI：
10.1021/acs.joc.9b01643
复制
发表时间：
2019-09-20
影响因子：
3.6
通讯作者：
Qiu, Guanyinsheng
中科院分区：
文献类型：
--
作者：
Liu, Renzhi;Li, Meng;Qiu, Guanyinsheng
本文报道了以2-炔基苯甲酰胺为起始原料，可切换合成异喹啉-1-酮和3-羟基异喹啉-1，4-二酮。该转化反应具有较好的产率和较宽的反应范围。用于提供异喹啉-1-酮和3-羟基异喹啉-1，4-二酮的合成开关通过使用N-2或O-2气氛来实现。反应机理研究表明，该反应是通过N-中心自由基6-内位二氮杂环化途径进行的。
In this work, switchable synthesis of isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione from 2-alkynylbenzamide is reported. The transformation works well with good yields and a broad reaction scope. The synthetic switch for providing isoquinolin-1-one and 3-hydroxylisoquinolin-1,4-dione is enabled by the use of a N-2 or O-2 atmosphere. Mechanism studies show that the reaction proceeds in a regioselective manner via a N-center radical 6-endo-dig aza-cyclization pathway.