Studies On The Synthesis Of Quinolines And Isatins Promoted By Radical Cation Salt

In this thesis, the reaction of N-cinnamylanilines and glycine amides were studied. The intramolecular cyclization of N-cinnamylanilines and glycine amides can occur smoothly under radical cation salt catalyzed conditions, giving quinoline and isatin derivatives respectively. The details are listed as follows:1、In catalytic amount of free radical cation salt TBPA+· induced conditions, the intramolecular cyclizaiton of N-cinnamylaniline compounds occurred, producing quinoline compounds. In this reaction: a peroxy radical cation intermediate could be generated by the coupling between O2 and TBPA+·, initiating the Csp3-H oxidation of N-cinnamylaniline compounds. The generated N-cinnamylaniline free radical could be oxidized to imine, which reacts with an aniline, yielding tetrhydroquinoline intermediate. After further aromatization, the 2-arylqunilines were afforded.2、In the presence of O2, a series of isatin compounds were achieved by radical cation salt TBPA+· induced reaction of glycine amide. Under the catalytic TBPA+· induced conditions, a ?-carbonyl free radical was generated by the activation of Csp3-H bond of glycine amide. The free radical could cyclize intrmolecularly. After further oxidation, isatin skeleton was constructed.