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Selective Heteroalkylations Of 1,2,3-Triazoles

Posted on:2021-05-24Degree:MasterType:Thesis
Country:ChinaCandidate:Z Y TangFull Text:PDF
GTID:2481306107494654Subject:Engineering
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1,2,3-triazoles,which are widely found in drug molecules,functional molecules,and metal ligands,have been broad applied in medical,materials and life science fields.Three consecutive nitrogen atoms are in the same ring,which make these compounds have unique physical or chemical properties.They are often used as aza-synthons in synthetic chemistry.This dissertation,based on properties of 1,2,3-triazoles,is focused on designing and completing selective heteroalkylations of 1,2,3-triazoles.This paper contains the following two chapters.In chapter one,three model reactions had been discussed: 1)The base promoted1,2,3-triazoles could be transformed into ketenimine intermediate that can react with nucleophiles,or cycloadditions.2)The metal catalyzed 1,2,3-triazoles could be converted into ?-imino metal carbenoid intermediate that would trigger follow cycloaddition reactions and X-H insertions(X = C,N,O).3)The metal-catalyzed and-free the alkylations of 1,2,3-triazoles.In chapter two,we discussed the advantages and shortcomings about the selective heteroalkylations of 1,2,3-triazoles firstly.Moreover a saturated heterocyclic alkylations of 1,2,3,-triazoles has been accomplished.The strategy addressed a regioselective issue of 1,2,3-triazole N1- and N2- position,offering an alternative opportunity for the amination/halogenation of saturnated heterocyclic compounds.Products can be obtained as potential activie molecular precursors,or we can lay the foundation for finding and discovering new drugs.Besides,the method was applied in the synthesis of RAD51 inhibitor by following one step reaction under the mild condition and easy manipulation.We described the reactivities of 1,2,3-triazoles in this dissertation.A new saturated heterocyclic alkylations of 1,2,3,-triazoles has developed to address the selective issue of N1 or N2,providing an alternative method for the amination/halogenation.
Keywords/Search Tags:1,2,3-triazoles, regioselectivity, saturated heterocycles, amination, alkylation
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