Copper-catalyzed Free Radical Reactions Of 2-azido-N-benzyl-N-phenylacrylamides With Togni’s Reagent And Zhdankin’s Reagent

This thesis discusses the tandem free radical reactions of 2-azido-N-benzyl-N-phenylacrylamides with trifluoromethyl radical/azidyl radical.It consists of two chapters.In the first chapter,the free radical reactions of azides are reviewed from the following three aspects:(1)The applications of free radical reactions in the synthesis of organic azides:(2)Organic azides as a source of aminyl radicals;(3)Organic azides as a source of iminyl radicals.The second chapter describes the research work during my graduate study,which is summarized as following:(1)The reaction of substituted 2-azido-N-benzyl-N-phenylacrylamides with trifluoromethyl radical was investigated by using Togni’ reagent as the trifluoromethyl radical source and Cul as catalyst.It was found that the addition of trifluoromethyl radical to the carbon-carbon double bond of 2-azido-N-benzyl-N-phenylacrylamides resulted in the formation of iminyl radicals,which then underwent cyclization to afford quinoxaline-2-ones.(2)By using Zhandkin’s reagent as the azidyl radical source,the reaction of substituted 2-azido-N-benzyl-N-phenylacrylamides with azidyl radical was investigated under the conditions similar to those mentioned above.The reactions produced two types of products:3-azidylmethyl-quinoxaline-2-ones and 3-cyano quinoxaline-2-ones.The studies not only provide new methods for the synthesis of functionalized quinoxaline-2-ones,but also shed light on the reactivity of α-(aminocarbonyl)iminyl radicals.