Copper-catalyzed radical reactions of 2-azido-N-arylacrylamides with 1-(trifluoromethyl)-1, 2-benziodoxole and 1-azidyl-1, 2-benziodoxole. Issue 13 (7th March 2016)

• Record Type: Journal Article
• Authors: Yang, Tonghao; Zhu, Haizhen; Yu, Wei
• Is Part Of: Organic & biomolecular chemistry. Volume 14:Issue 13(2016)
• Page Start: 3376
• Page End: 3384
• Publication Date: 2016-03-07
• Subjects: Chemistry, Organic -- Periodicals; Bioorganic chemistry -- Periodicals; Chemistry, Physical organic -- Periodicals; 547
• DOI: 10.1039/c6ob00226a
• Languages: English
• ISSNs: 1477-0520

Abstract

Abstract : The tandem addition/cyclization reactions of 2-azido- N -arylacrylamides with 1-(trifluoromethyl)-1, 2-benziodoxole and 1-azidyl-1, 2-benziodoxole-derived trifluoromethyl radicals and azidyl radicals were investigated. Abstract : The reactions of 2-azido- N -arylacrylamides with trifluoromethyl radicals and azidyl radicals were investigated by using Togni's reagent and Zhdankin's reagent as the source of these radicals. Under the catalysis of CuI, Togni's reagent was firstly converted into the trifluoromethyl radical, which then reacted with 2-azido- N -arylacrylamides to afford the corresponding α-(arylaminocarbonyl)iminyl radicals. The cyclization of the iminyl radicals delivered quinoxalin-2(1 H )-one products in moderate yields. A similar reaction took place between 2-azido- N -arylacrylamides and the azidyl radical. In the latter cases, the reaction produced 3-azidomethyl and 3-cyano-subsituted quinoxalin-2(1 H )-ones. This study not only helps elucidate the factors influencing the cyclization of α-(arylaminocarbonyl)iminyl radicals, but also provides a new approach towards quinoxalin-2-ones.