Base-controlled [3+3] cycloaddition of isoquinoline N-oxides with azaoxyallyl cations. Issue 68 (3rd August 2016)

• Record Type: Journal Article
• Authors: An, Yuanyuan; Xia, Hongguang; Wu, Jie
• Is Part Of: Chemical communications. Volume 52:Issue 68(2016)
• Page Start: 10415
• Page End: 10418
• Publication Date: 2016-08-03
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c6cc03650c
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : A base-controlled [3+3] cycloaddition reaction of isoquinoline N -oxides with azaoxyallyl cations is developed, leading to 1, 11 b -dihydro-[1, 2, 4]oxadiazino[3, 2- a ]isoquinolin-2(3 H )-ones and 2-(isoquinolin-1-yloxy)acetamides, respectively. This transformation proceeds through an azaoxyallyl cation generated in situ from α-bromohydroxamate. Abstract : A base-controlled [3+3] cycloaddition reaction of isoquinoline N -oxides with azaoxyallyl cations is developed. 1, 11 b -dihydro-[1, 2, 4]oxadiazino[3, 2- a ]isoquinolin-2(3 H )-ones are obtained when isoquinoline N -oxides are treated with α-halohydroxamates in the presence of sodium carbonate, while 2-(isoquinolin-1-yloxy)acetamides are unexpectedly produced when the base is changed to cesium carbonate. This transformation proceeds through an azaoxyallyl cation generated in situ from α-bromohydroxamate, and the [3+3] cycloaddition reaction is the key step for the final outcome.