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Study On Passerini Reaction Of Isonitrile Compounds Driven By DTBP

Posted on:2021-01-12Degree:MasterType:Thesis
Country:ChinaCandidate:Y ZhangFull Text:PDF
GTID:2381330626963528Subject:Organic Chemistry
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?-Acyloxyamides are a kind of multifunctional compounds,which widely occur in natural products and pharmaceutical drugs as the privileged skeletons with important biological and pharmaceutical activities.In addition,these compounds are also important intermediates in organic synthesis and are widely used in the synthesis of many important oxygen-containing and nitrogen-containing compounds.Therefore,the synthesis and the application of ?-acyloxyamides have attracted widespread attention.Isonitrile compounds are a very important class of organic synthons for the construction of various nitrogen-containing compounds and have been widely used in organic chemistry,medicinal chemistry,natural product chemistry,and materials chemistry.Therefore,the research on the application of isonitrile compounds has received widespread attention.Among the various reactions,the multicomponent reaction involving isocyanide has been a research focus in the field of isocyanide chemistry due to the advantages of high regioselectivity,strong chemical selectivity,and high atomic utilization rate.As one of the multi-component reactions,Passerini three-component reaction(P-3CR)generally refers to the reaction of three-component coupling of aldehyde,isonitrile and carboxylic acid to synthesize ?-acyloxyamide.In this field of research,Passerini reactions using aldehydes instead of carboxylic acids are not only extremely rare,but the reported methods are only suitable for alkyl isonitriles.Therefore,exploiting new Passerini reaction involving two molecules of aldehyde and one molecule of isonitrile is highly desirable.In this paper,using isonitriles as the starting material together with developing a new Passerini reaction of isonitrile as the core,a DTBP-promotoed Passerini three-component reaction of two molecules of aldehyde and one molecule of isonitrile was developed.The method has many advantages such as wide substrate scope,simple operation,milde reaction conditions.The experimental results not only provide a simple and effective new method for the synthesis of ?-acyloxyamide compounds,but also lay a solid foundation for the application of a new type of peroxide-driven Passerini three-component reaction in organic synthesis.
Keywords/Search Tags:Passerini reaction, isonitriles, aldehydes, DTBP, ?-acyloxyamides
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