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Research On Synthesis Of Heterocyclic Compounds By Peroxides

Posted on:2021-12-08Degree:MasterType:Thesis
Country:ChinaCandidate:N FengFull Text:PDF
GTID:2481306569496334Subject:Chemistry
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Organic peroxides refer to derivatives in which one or two hydrogen atoms of hydrogen peroxide are replaced by organic groups.The average bond energy of peroxy bonds(-O-O-)is only 30?50 kcal/mol.Because the lower bond energy makes organic peroxides have poor thermal stability,they have strong oxidizing properties.With the development of organic peroxide preparation technology,it has received extensive attention in organic chemical reactions.Benzolactone refer to compounds containing a benzo-?-pyrone structure.This paper proposes a method for constructing Benzolactone in a non-metallic system with simple operation,mild conditions and low cost.By using the phthaloyl peroxide/cesium iodide system,a blue light emitting diode at 420 nm The Benzolactone were synthesized under irradiation,and 20 Benzolactone with different substituent groups were obtained with a yield of 22?99%.This reaction can be used to construct important organic synthesis intermediates containing lactone skeleton;based on the analysis and discussion of experimental results,the reacti on mechanism of radical anion intermediates further forming corresponding lactone products through cyclization reaction is proposed.Nitrogen-containing heterocycles are a ubiquitous structural unit in natural products,and they are also widely used as synthetic intermediates in the synthesis of various complex organic molecules.In this thesis,9 kinds of chlorinated nitrogen heterocyclic compounds with a yield of 40?85% were synthesized by cyclopentyl malonyl peroxide/palladium acetate metal catalyst system with amine containing non-activated olefin as the substrate,and the yield It is 69% of acetyl substituted nitrogen heterocyclic compounds,which realizes the construction of nitrogen-containing heterocyclic systems containing different substituent grou ps.Under optimal conditions,the application of this reaction in the field of asymmetric catalytic synthesis was explored,and products with up to 26% enantiomeric excess were obtained.By investigating the literature and summarizing the experimental facts,it is speculated that the reaction promotes the rapid and efficient synthesis of nitrogen-containing heterocyclic compounds through the Pd(II)-Pd(IV)catalytic cycle mechanism.
Keywords/Search Tags:phthaloyl peroxide, cyclopentyl malonyl peroxide, heterocyclic compound, cyclization reaction
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