Design And Synthesis Of N-substituted1,2,3-triazole Ligands Together With Their Applications In Click Chemistry

Click chemistry is a new synthetic method of combinatorial chemistry. It is widelyused in creating lead compounds libraries, developing new drugs, synthesizing polymersand so on，owing to the available raw materials, simple operations, mild reactionconditions, high yields and good selectivity. However, the most classical click chemistry iscopper(I)-catalyzed azide-alkyne cycloaddition reaction used to synthesize1,4-substituted-1,2,3-triazoles.With the rapid development of Cu(I)-catalyzed azide-alkyne cycloaddition reaction,much more attention is paid to develop more efficient, cleaner, generally applicable andhighly selective catalytic system, especially the Cu(I)/ligand catalytic system. It tends to bethe hot topic. In this thesis, we designed and synthesized a series of N-pyridinesubstituted-1,2,3-triazole ligands, and succeed in applying them to click chemistry. Theligands can assist copper iodide to efficiently catalyze azides and alkynes to synthesize1,4-disubstituted-1,2,3-triazoles.When optimizing the reaction with N-piridine Cu(I)/substituted-1,2,3-triazolecatalytic system and choosing the cycloaddition reaction of the reaction of benzyl azideand phenylacetylene as template, we explored the catalytic activity of N-pyridinesubstitued-1,2,3-triazole ligands assisting Cu(I) respectively and the influence of differentsolvents, temperature and catalytic loading to the Cu(I)/N2-pyridinesubstituted-1,2,3-triazole catalytic system. And we synthesized tweenty-seven differentkinds of1,4-disubstituted1,2,3-triazoles with mild conditions, good selectivity, highyields and wide application. Some special substrates such as aminos, hydroxys andsulfonyls are included. All of the products were characterized by HRMS,1H-NMR and13C-NMR.In addition, we studied the [3+2] cycloaddition reaction mechanism of N-pyridinesubstituted-1,2,3-triazole ligand assisting copper(I) catalyzing terminal alkynes and azides,basing on the synthesis and structure research of copper(I)-ligand2complexes.