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Regioselective Synthesis Of Nitrogen-containing And Oxygen-containing Heterocyclic Compounds

Posted on:2015-09-06Degree:MasterType:Thesis
Country:ChinaCandidate:F DouFull Text:PDF
GTID:2191330479983891Subject:Organic Chemistry
Abstract/Summary:PDF Full Text Request
Nitrogen-containing and oxygen-containing heterocyclic compounds are an important class of organic compounds. These compounds are widely used in many fields of medicine, pesticide and organic materials, and in human life and industrial production. Consequently, their syntheses have received more attention in chemical community. So development of efficient, mild and simple approach for the synthesis of nitrogen-containing and oxygen-containing heterocyclic skeleton has been the focus of chemistry.This paper studies the synthesis of these heterocyclic compounds using homoallyl alcohols or amines as the starting material under mild conditions in a simple manner.The first chapter introduces the advance of the synthesis of oxygen-containing and nitrogen-containing heterocyclic compounds through Prins cyclization reaction, and also provides an overview of the topic of this article based on the significance and innovation.The second chapter describes the regioselective synthesis of 2, 2-dimethyl-tetrahydrofuran derivatives using α-prenylated alcohols as the starting material through Prins cyclization reaction. The advantages of this method includes high regioselectivity, the empolyment of metal-free catalyst and the mild reaction conditions.The third chapter describes the synthesis of 3,3,4- trimethyl hydrogenated quinoline derivatives using homoallyl amine containing γ-prenyl fragment as the substrate in the presence of sulfuric acid via intramolecular cyclization. Remarkably, the presented method features short reaction time, excellent yield and simple experimental procedure.The fourth chapter describes the synthesis of 5,5-dimethyl-benzazepine derivatives using the homoallyl amine containing α-prenyl fragment as the substrate in the presence of catalytic sulfuric acid. The reaction react in a simple and efficient way to afford seven-membered heterocyclic structure. Further investigations are in progress to evaluate the process with a broader range of the substrates.
Keywords/Search Tags:Nitrogen and oxygen heterocyclic, Homoallyl compounds, Regioselectivity
PDF Full Text Request
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