Studies On The Synthesis And Application Of Iodo-1,2,3-triazole

1,2,3-triazoles are important structural moieties in drug synthesis, bioconjunction, and materialsscience, benefiting from their ease of synthesis and chemical stability. The copper (I)-catalyzed azide-alkyne cycloaddition (CuAAC) is a reliable means for the synthesis of1,4-disubstituted-1,2,3-triazoles.The general and regioselective synthetic methodology to the1,5-regioisomers, by contrast, are not welldeveloped.On the other hand, water is the solvent of choice for nature in all biosynthetic routes, which has theadvantage of being abundantly available, nontoxic, nonflammable and inexpensive, With water as solvent(in/on water), remarkable reactivity and selectivity could also be achieved due to special solvation andmolecular assembly modes. In this context, reactions in/on water have attracted great interest in drug design,materials science, and biological processes.Therefore, based on our previous work, this dissertation has carried out the methodologies research ofmultisubstituted and1,5-disubstituted1,2,3-triazoles. The innovations include:(1) multicomponentsynthesis of5-iodo-1,2,3-triazoles in the pure water medium.(2) synthesis of the dual-functional4-TMS-5-iodo-1,2,3-triazoles, following the development of a new methodology to synthesize1,5-disubstituted1,2,3-triazoles and1,4,5-trisubstituted1,2,3-triazoles. The details are shown as follow:1. Review of the development of iodination and its application in the field of bio-labeling, drugsynthesis; review the latest progress on synthesis methodology of1,4,5-disubstituted1,2,3-triazoles andit’s application in drug design.2. Developed a new method of the synthesis of5-iodo-1,2,3-triazoles in the presence of CuI/selectflulor/DIPEA in water with teminal alkyne, azide and tetrabutylammonium iodide as startingmaterials. The high tolerance of various sensitive groups and high chemoselectivity revealed the potentialof this method in organic synthesis and drug discovery.3. Developed a new route of the synthesis of5-aryloxy-1,2,3-triazoles and5-thiopheno-1,2,3-triazoles by catalytic system of CuBr/ethyl2-cyclohexanonecarboxylate, with the4-TMS-5-iodo-1,2,3-triazoles as starting materials. 4. Developed a new route to synthesize1,4,5-trisubstituted1,2,3-triazoles from4-TMS-5-iodo-1,2,3-triazoles in the presence of Pd/Cu catalytic system.