90841-79-5Relevant academic research and scientific papers
Synthesis of Phenanthridine and Quinoxaline Derivatives via Copper-Catalyzed Radical Cyanoalkylation of Cyclobutanone Oxime Esters and Vinyl Azides
Kong, Xianqiang,Li, Guodong,Liang, Qi,Lin, Long,Xu, Bo
, p. 1948 - 1952 (2021)
A copper-catalyzed radical cyclization of cyclobutanone oxime esters and vinyl azide is described. This method provides facile access to cyanoalkyl-substituted phenanthridines and quinoxalines with excellent isolated yields. Moreover, these reactions proceed under mild conditions with a board substrate scope and excellent functional group tolerance.
Electron-Catalyzed Fluoroalkylation of Vinyl Azides
Mackay, Emily G.,Studer, Armido
, p. 13455 - 13458 (2016/09/13)
The transition-metal free fluoroalkylation of vinyl azides is herein reported. This operationally simple reaction employs the Togni reagent as a CF3source, Bu4NI as an initiator, and occurs under electron catalysis. A range of readily prepared starting materials are functionalized using this approach to produce both phenanthridines and quinoxalin-2-ones.
Copper-catalyzed radical reactions of 2-azido-N-arylacrylamides with 1-(trifluoromethyl)-1,2-benziodoxole and 1-azidyl-1,2-benziodoxole
Yang, Tonghao,Zhu, Haizhen,Yu, Wei
, p. 3376 - 3384 (2016/04/09)
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(1H)-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(1H)-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.
