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Synthesis And Characterization Of1-allenic Or1-styryl-substituted-l,2,3-triazoles

Posted on:2014-04-18Degree:MasterType:Thesis
Country:ChinaCandidate:A Y HeFull Text:PDF
GTID:2251330401487685Subject:Organic Chemistry
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1,2,3-Triazole compounds, a class of nitrogen-containing heterocycliccompounds with biological activity, multi-purpose, have been widely used inagriculture, industry, medicinal chemistry and materials chemistry and other fields. Inrecent years, chemical researchers pay more attention to the development novel1,2,3-triazole compounds. In this paper, two kinds of novel1,4-disubstituted-1,2,3-triazole compounds such as1-allenic-4-substituted-1,2,3-triazoles and1-(E)-styryl-4-substituted-1,2,3-triazoleswere synthesized and characterized. The advantages of these syntheticmethodologyies include mild reaction conditions, straightforward operation and highselectivity, as well as good yields.The main work of the paper is as follows:Firstly, three-component reaction of2,3-dibromopropylene, sodium azide withterminal alkyne in the Cu(I)/PEG-H2O catalyst/solvent system through substitutionreaction and Huisgen1,3-dipolar cycloaddition reaction successively yielded a seriesof1-(2-bromopropenyl)-4-substituted-1,2,3-triazoles compounds, which was furthertreated with NaH to afford1-allenic-4-substituted-1,2,3-triazole compounds in goodyields (73-93%).Secondly, one-pot reaction of2-azido-1-iodo-ethylbenzene, terminal alkyne andtriethylamine in the Cu(I)/PEG-H2O catalyst/solvent system formed1-(E)-styryl-4-substituted-1,2,3-triazoles in78-92%yields.
Keywords/Search Tags:1,4-disubstituted-1,2,3-triazoles, Cu(I)/PEG-H2O catalyst/solvent system, one-pot reaction, Huisgen1,3-dipolar cycloaddition, 1-allenic, 1-(E)-styryl
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