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The Synthetic Study Of Oxygenated Heterocyclic Compounds With Diaryliodonium Salts

Posted on:2019-02-01Degree:MasterType:Thesis
Country:ChinaCandidate:G X Z LiuFull Text:PDF
GTID:2381330590451710Subject:Chemistry
Abstract/Summary:PDF Full Text Request
Hypervalent iodine compounds have became the focus of attention of organic chemistry researchers in recent years because of their mild reaction condition,high activity,and easy preparation and preservation.As reagents capable of providing various functional groups in methodological studies,diaryliodonium salts have excellent performance in the synthesis of heterocyclic compounds.Diaryl iodonium salts are capable of forming aryl cations in reaction with various nucleophilic substrates in the presence of metal catalysts.Some work reported in recent years shows that the electrophilic arylation of diaryliodine can not only achieve the arylation of the substrate but also conduct cyclization to form a new cyclized product.Due to the nucleophilic attack on the aryl cations formed by the diaryl high-valent iodine under the action of the metal catalyst,its ortho-position carbon atom still has certain electrophilicity,and thus can be nucleophilic attacked and cyclized.Heterocyclic compounds exist widely in nature.Many natural molecules and functional molecules contain heterocyclic skeletons.Therefore,methods for constructing heterocyclic compounds have always been a research focus in organic synthesis methodologies.Heterocyclic compounds have a wide range of applications in fields such as biomedicine and materials science.Therefore,the method of constructing heterocyclic compounds has always been a research focus in organic synthesis methodology.The research on the synthesis of nitrogen-containing heterocyclic compounds has been reported in recent years.However,there are relatively few studies on the synthesis of oxygen-containing heterocyclic compounds.In this paper,diaryliodine compounds and other readily available compounds are used to synthesize various functional heterocyclic compounds.The reaction is convenient and mild,the steps are simple and economic,and the free control of substituents can be achieved.The following groundbreaking results have been achieved:1.Designing the intramolecular cyclization of diaryl high-valent iodine and methyl salicylate compounds to achieve the synthesis of ketene-based compounds through simple and readily available raw materials,providing a new synthesis of ketene-based compounds.The method,at the same time,achieves the free regulation of the t-ketone substituent.2.The reaction of ?-hydroxycarboxylic acid methyl ester substrate with biaryl high-valent iodine compound was designed to realize the synthesis of benzopyrone compounds.Provides new ideas for the synthesis of oxygenated benzoheterocycles.The resulting heterocyclic compound was subjected to derivatization experiments to verify the practical utility of this product.In this dissertation,diaryl high-valent iodonium salts and various simple substrates were used to react to construct heterocyclic compounds,which provided a new idea for the synthesis of heterocyclic compounds.The reaction has the characteristics of economical conditions and achieved product substitution.Freedom of regulation.
Keywords/Search Tags:Diaryliodonium salts, Xanthone, benzopyrone, electrophilic arylation
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