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Investigations On The Selective Oxidation Reaction Of The Tertiary Amines

Posted on:2014-06-16Degree:MasterType:Thesis
Country:ChinaCandidate:P DuFull Text:PDF
GTID:2251330401982652Subject:Industrial Catalysis
Abstract/Summary:PDF Full Text Request
Selective oxidation of the tertiary amine is a challenge and hot topic in modern synthetic chemistry. It caused great interest in the field of biochemistry and organic chemistry, and a series of useful pharmaceutical intermediates by this method were synthesized in convenience. Through chemical transformations of structural varieties of tertiary amines, they can give lots of different and chemical specialties of iminium. Thus, it has great value to carry out this kind of research.The dissertation consist of three chapters. The first chapter is a review on the selective oxidation of the tertiary amine. Method and significance of the different oxidants for the selective oxidation of the tertiary amine were introduced.In the second part, the hydration of propargyl amine promoted by diethyl azodicarboxylate (DEAD) is discussed. Promoted by DEAD, a novel and highly stereoselective synthesis of cis-β-enaminones via oxidative dehydrogenation and hydration of the substituted propargylamines was realized. The reaction was carried out in the yield of55%with1.0mmol1-(3-phenylprop-2-ynyl)piperidine,1.5mmol H2O and1.5mmol DEAD under room temperature. The scope of substrates was subsequently examined.In the third part, the photoredox of tertiary amine for the synthesis of bis-1,3-dicarbonyl compound was studied. The reaction provided an efficient synthetic procedure for the preparation of methylene-bridged1,3-dicarbonyl compounds through an aerobic photocatalytic oxidative coupling reaction between1,3-dicarbonyl compounds and N,N-dimethylcyclohexylamine. The reaction was carried out in the yield of90%with0.5mmol%Ir(ppy)3,1.8mmol N,N-dimethyl cyclohexylamine and1.0mmol dibenzoylmethane in DCE under45W Incandescent lamp and room temperature. The scope of substrates was subsequently examined.
Keywords/Search Tags:oxidation, tertiary amine, DEAD, enaminone, photoredox
PDF Full Text Request
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