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Nitrogen Heterocyclic Compounds Are Synthesized Through The Radical Addition Of Carbon-carbon Double Bonds

Posted on:2019-07-31Degree:MasterType:Thesis
Country:ChinaCandidate:X X LiFull Text:PDF
GTID:2431330548996033Subject:Organic Chemistry
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Heterocyclic compounds which contain nitrogen,oxygen,sulfur or other heteroatoms exist in natural products and molecular fragments of drugs,and they are often used in various fields such as biology,medicine,pesticide,insecticide and dyes.Therefore,heterocyclic compounds have important research value.In recent years,the strategy of synthesizing heterocyclic compounds by free radical addition to alkene cyclization has been widely used.Especially,free radicals are generated by transition metal-free catalysis under heating conditions;or in the visible light,using organic dyes as photocatalysts to synthesize heterocyclic compounds.In this paper,I will introduce the research progress of synthetic heterocyclic compounds in detail and carry out a series of studies on the free radical addition cyclic reactions of olefins.This thesis mainly includes the following two aspects of research content:1.Addition of nitrogen dioxide to carbon-carbon double bond followed by a cyclization to construct nitromethylated Isoquinolinediones.We used nitrogen dioxide as a nitro source,1,4-dioxane as a solvent,and then heated at 80 ? for 12 hours,we can achieved nitration products.The reactions are carried out under smooth conditions,and do not need any catalyst,the reaction conditions can tolerate a wide range of functional groups,and all got moderate to good yields.Simultaneously,the product can be converted to aminomethyl or hydroxy-substituted heterocyclic derivatives by simple reduction.2.Photoredox Catalysis:Construction of Polyheterocycles via Alkoxycarbonylation/Addition/Cyclization Sequence.We used 5 W white LEDs as the light source,Eosin Y as a photocatalyst,Butylhydroperoxid as an oxidant and carbazate as alkoxyl radical source,and then react under light for 36 hours.We achieved synthesize ester-functionalized phenanthridine derivatives,through the free radical addition cyclization reaction.The reaction conditions are mild,Free-radical sources are cheap and readily available,while substrates have good compatibility.In addition,to determine the configuration of the products,we performed X-ray diffraction.
Keywords/Search Tags:Metal-free reaction, free radical addition cyclization, isoquinolinedione, phenanthridine compound
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