Studies On The CuI-catalyzed Photocyclization Of Aryl Azides

This thesis deals with the studies on organic azides. It is divided into two chapters.Chapter1describes basic properties, preparation methods and main chemistry reactions of organic azides. It focuses on their photochemiscal reactions including cycloadditions, nitrene chemistry, insertion reactions, rearrangement reactions and metal-catalysis reactions, and the application of these reactions in the organic synthesis.Chapter2reports my research works on the photochemistry of organic azides. Firstly, the CuI-catalyzed photoreaction and thermal reactions of3-(2-azido-benzylidene)-lactams have been investigated. The studied lactams are3-(2-azidobenzylidene) indol-2-ones,3-(2-azidobenzylidene)pyrrol-2-ones,4-(2-azido-benzylidene)pyrazol-5-ones,4-(2-azidobenzylidene)-2-phenylisoquinoline-1,3(2H,4H)-dione, and5-(2-azido benzylidene)-1,3-dimethylpyrimidine-2,4,6(1H,3H,5H)-trione. A new method for the synthesis of fused indole compounds, such as indolo[3,2-c]quinolin-6-ones, pyrido[4,3-b]indol-1-ones, pyridazino[4,5-b]indol-1-ones, dihydroindolo[3,2-d][2]benzazepin-5,7-dione, and [1,3]diazepino[5,6-b] indole-1,3,5-trione, has been developed by the photochemical and thermal cyclization-rearrangement reactions. It is an efficient method that is embodied under mild reaction condition and in high reaction yields. Secondly, the studies on the photoreaction of other3-(2-azidobenzylidene)-substituted compounds, such as1-(2-azidobenzylidene)-1H-indenes and2-(2-azidobenzylidene)-ones have been introduced. Benzocarbazoles and other fused indole derivatives have also been synthesized.