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A Study on Heterocyclic Ketene Aminals and the Synthesis and Structural Characteristic of Its Derivatives

Author: YouJun
Tutor: LiuBo
School: Harbin University of Science and Technology
Course: Materials Physics and Chemistry
Keywords: Heterocyclic ketene shrink amine Synthesis method Reaction Mechanism
CLC: O626
Type: Master's thesis
Year: 2004
Downloads: 125
Quote: 1
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Abstract


Heterocyclic enone condensing the amine is a very versatile synthon heterocyclic compound . Conducted a detailed study of the preparation , structural characteristics , and the reaction characteristics , and its application in organic synthesis , etc. condensed heterocyclic ketene amine . The in-depth study of this reaction is the main subject of this dissertation . This thesis work mainly include two parts : ( 1 ) systems studied of heterocyclic ketene condensing amine synthesis method , as well as heterocyclic ketene condensing amines with a series of nucleophilic addition reactions of electron deficient reagent ; (2) Synthesis the four novel heterocyclic ketene condensing amine derivative, and conducted a detailed analysis of their structure , the establishment of the new ways of the amine derivative of a synthetic heterocycloalkenyl . The first part : 1 . Detailed description of the latest of heterocyclic ketene reduction amine synthesis . Heterocyclic system shrink electrophilic addition reaction of amines : miscellaneous change ketene shrink amine is a unique hybrid ene component , with a series of α, β- unsaturated compounds , azo ester as well as activation the addition reaction of the carbonyl compound after azepin ethylenically way . Heteroaryl exchange ketene condensing amine as the two nucleophiles substituted reaction can occur regiospecific alkylation reaction , region selection acylation, glycosylation reaction , halogenation , nitration reaction . Cycloaddition reaction occurred with 1,3 - dipolar reagents . Heterocyclic ketene condensing the amine with a nitrile ylides reaction can only get 1:1 nucleophilic addition product , the nucleophilic reaction can occur at the α-carbon atom , to produce C- substituted product , can also occur in the heterocyclic secondary amine groups generated N-substituted product. Part II: enone condensing substituted heterocyclic amine with ethyl bromoacetate reaction fluorobenzoyl or heterocyclic aroyl , high yield diazabicyclo [ 330 ] or diazabicyclo [ 430 ] derivatives. The reaction mechanism was discussed in the text , and were used to characterize the structure of the product .

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Heterocyclic compounds
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