Radical N-centered 6-endo aza-cyclization of 2-alkynylbenzamide

来源 :中国化学会第十六届全国有机合成化学学术研讨会 | 被引量 : 0次 | 上传用户:FSACN
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  Considering its ubiquity of N-containing compounds,various N-containing synthons were developed for accordingly.Among them,N-center radical species was a history-long yet many-issues-unsettled topic in the field of organic chemistry.As such,tremendous efforts were made in past decades,thus enabling signficant progress of amidyl-nitrogen radical and imine-nitrogen radical chemistry.1 To the best of our knowledge,amidyl nitrogen-radical could be achieved through a metal-free process,metal catalysis and photocatalysis etc.In our works,we have developed a copper-catalyzed radical cyclization of 2-alkynylbenzamide for the synthesis of isoquinolin-1-one under N2 atmosphere.2 Interestingly,the above strategy could be used to the formation of 3-hydroxylisoquinolin-1,4-diones as well when the reaction was conducted in the presence of O2 balloon.Mechanism studies showed that the reaction proceeds in a regioselective manner via an N-center radical-based 6-endo-dig aza-cyclization pathway.
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