CuCl₂/Zn-catalyzed Synthesis Of Indole-triazole Derivative And Activity Reserach

N-containing heterocycles, for its extensive application and good biological activity, have been developed into many new kinds of pesticides and medicines. In relevant fields, there has been a hot research on the synthesis and structural optimization of such N-containing heterocycles. As the bioisostere of1,2,4-triazole,1,2,3-triazole has high aromatic stability and extensive biological activity, such as antibacterial property and antiviral property.1,3-Dipolar cycloaddition reaction of organic azide and alkyne, catalyzed by copper(I), which was found by Sharpless and Meldal groups, is also known as Huisgen-click reaction. This method makes it convenient to synthesize1,2,3-triazole economically. However, most of the catalytic systems need to be added with reducing agents, alkalis or ligands, and most of the reaction is carried out in organic solvents or organic-water mixed solvents, sometimes exposed under high temperature, which offends the concept of green chemistry. In nowadays, environmental protection is becoming more important, so it’s of great significance to find a new synthetic method, which is both efficient and environmental friendly.In this paper, the development of green chemistry and click chemistry is reviewed in chapter1. In chapter2, in order to find an efficient and simple catalyst for Huisgen-click reaction, the reaction of phenyl propargyl ether with benzyl azide was selected as the model reaction. We have tried to optimize the reaction conditions from five aspects:solvent, catalyst, catalyst amount, reaction temperature, and the influence of ultrasound. After a lot of experiments, an efficient protocol for the synthesis of a series of1,2,3-triazole derivatives was established: CuCl2(10mol-%)/zinc powder (10mol-%) as catalyst and water as solvent reacting under room temperature. And a series of1,4-disubstituted1,2,3-triazole derivatives have been synthesized based on the optimized conditions. The results showed that this type of catalyst system has a broad scope of application. In summary,15compounds have been synthesized, all of which haven’t been reported before.In chapter3, a series of indole-1,2,3-triazole compounds are synthesized under the optimized conditions. We have synthesized26new indole derivatives. All of the compounds are characterized by IR, MS and NMR. The key step of this reaction is modify indole with azides or terminal alkynes. The successful synthesis of these indole-l,2,3-triazole compounds proves the feasibility of CuCl2/Zn catalyst system for Huisgen-click reaction.In chapter4, some of the synthesized indole derivatives are selected for further biological activity testing. Finally, chili anthrax pathogen, cotton physalospora pathogens, tomato bacterial canker are chosen to tested the antibacterial spectrum of these compounds through antimicrobial tests in vitro. The preliminary test results have showed that these compounds have certain inhibitory effect for fungi, and the best restraint is up to50%within72h, and there is no inhibitory effect for bacteria. The results have formed principal foundation for further studies.