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Synthesis And Properties Of Novel 1,2,3-Triazole Compounds

Posted on:2018-02-21Degree:MasterType:Thesis
Country:ChinaCandidate:Q Q HuFull Text:PDF
GTID:2371330542970311Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
1,2,3-triazole are a class of very important nitrogen-containing heterocyclic compounds and have important applications in many areas.In medicine chemistry,1,2,3-triazole compounds as amide bond bioisostere and very stablein the biological metabolism which makes 1,2,3-triazole widely used in the design of new drug molecules as building block,and some of 1,2,3-triazoles compounds has showedgood biological activityin many aspects.In terms of material chemistry,based on“click chemistry”strategy,1,2,3-triazole skeletons can be introduced as a stable linker into some polymer materials,and some functional materials with unique properties have been developed.In the organic chemistry,under certain conditions,such as Rh catalyst,1,2,3-triazoles canremovel of nitrogen to get Rh carbene which for syntheszeunique structural compounds through further reaction.At the some time,because of the large eledtron density around the triazoles heterocyclic,1,2,3-triazoles can be well coordinated with many metals.The novel metal complexes obtained by these ligands have unique applications in optical,electronic,catalysis,antibacterial and materials.Although 1,2,3-triazole compounds have a wide range of applications,there are no report of 1,2,3-triazole compounds were directly extracted from natural products.All of 1,2,3-triazoles compounds and their derivatives are artificially synthesized by chemical methods.1,2,3-triazole’great application prospects which make a research hotspot in present chemistry.The general methods of synthesis 1,2,3-triazoles is through the[3+2]cycloaddition reaction of unsaturated hydrocarbons and organic azidesand usually obtained 1,4-disubstituted,1,5-disubstituted,or 1,4,5-trisubstituted-1,2,3-triazole through this way.While the other 1,2,3-triazoles,NH-1,2,3-triazole and N2-substituted-1,2,3-triazole,there are less synthetic methods relatively.It is a meaningful and challenging work to find a efficient method for the synthesis of NH-1,2,3-triazole in a mild condition.On this basis,through the post-functionalizationofNH-1,2,3-triazoletosynthesisofnovel N2-substituted-1,2,3-triazole compounds are also important.In this paper,we used aryl nitroolefins and sodium azide as raw materials and aluminum trichloride as catalyst to synthesis of NH-1,2,3-triazoles efficiently in mild reaction condition.Then,we use aryl aldehydes,nitro compound and sodium azide as raw materialsand,aluminum trichloride as catalyst,through the three-component reaction in one-pot to obtain NH-1,2,3-triazoles more convenient.Especially,some of synthesized 1,2,3-triazoles is difficult to be synthesized by other methods.In the third part of the paper,we report adirect P2O5-mediatedsynthesis of diverse sulfur-containing triazoles via alkylation of NH-1,2,3-triazoles with dimethyl sulfoxide.So far,N2-substituted sulfur-containingtriazoles have rarely been reported.
Keywords/Search Tags:NH-1,2,3-triazole, aluminum trichloride catalyzed, three-component reaction, N~2 alkylation
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