Copper Catalyzed Synthesis Of 5-Amino-[1,2,3]triazolo[5,1-a]isoquinolines

1,2,3-triazoles are one kind of significant N-fused five-membered rings compounds, and their syntheses and applications have been reported frequently, especially after the development of click chemistry. However, 1,2,3-triazole-fused heterocyclic compounds are rare so far, but it was found that some of 1,2,3-triazole-fused heterocycles exhibit unquie properties, especially in the field of medicine, pesticide, polymer materials, etc. For example, it has been found some 1,2,3-triazole-fused heterocyclic compounds show pharmaceutical activities, such as anti-tumor, anti-HIV, antiviral. In this thesis, we developed a copper-catalyzed cascade strategy for the synthesis of 5-amino-[1,2,3] triazolo [5,1-a] isoquinoline derivatives, furthermore, we also reported the fluorescence properties of the responding compounds with some metal ions.The thesis contains the following sections:In the first chapter, the synthetic methods of 1,2,3-triazole fused heterocyclic compounds and their applications in the field of chemistry, materials, biology, medicine were reviewed.In the second chapter, the synthesis of 5-(2-bromoaryl)-1H-1,2,3-triazoles were reported, the methods include that condensation of nitroalkenes react with sodium azide, and the condensation of alkyne with sodium azide.In the third chapter, a novel synthsis of 5-amine-[1,2,3]triazolo[5,1-a]-isoquinolins via copper(I) catalyzed cascade reactions in one-pot was reported. Firstly, the reaction conditions were optimized, including the screening of solvents, bases, catalysts, ligands and the reaction temperature; Secondly, a total of 24 kinds of the 5-amine-[1,2,3]triazolo [5,1-a]-isoquinolins were synthesized under the optimization reaction condition; Thirdly, the reaction mechanism were also investigated by some control experiments.In the last chapter, the fluorescence properties of 5-amino-[1,2,3]triazolo[5,1-a] isoquinoline derivatives with metal ions were detected. It was found that some compounds can interact with Hg2+ and Cu2+. In addition, we set up a method using ethyl 5-amino-[1,2,3]triazolo[5,1-a]-isoquinoline-6-carboxylate fluorescence to detect mercury ion.