One Pot Construction Of Amide And 4-Aminoquinoline Derivatives

In organic chemistry,amide compounds are a very important class of compounds.Many natural products,agricultural chemicals,synthetic products and polymers contain amide bonds,and they can also be used as potential synthetic precursors of drugs.The formation of amide bonds is one of the most common transformations in organic synthesis methodology.For many years,the synthesis and modification of amide compounds has never stopped.Although there are many reports on the synthetic strategies of amide compounds,it is still necessary to develop a simpler and more efficient methods.Therefore,in this thesis,we provide a new method for directly synthesizing amide derivatives using simple and readily available substrates without transition metals.Nitrogen-containing aromatic heterocyclic compounds are a branch of heterocyclic compounds,which are widely exist in nature and have a very important application in various fields.Quinoline compounds are typical nitrogen-containing aromatic heterocyclic compounds,which are widely found in natural products and synthetic organic compounds.It has been discovered that quinoline derivatives are not only used as pharmaceutical intermediates because of their good biological activity,but also widely used in metallurgy,dyes,rubber,important raw materials for agrochemical industries,polymer materials and fluorescent probes,and so on.Since it was first synthesized,the research on the synthetic methodology of quinoline and its derivatives has attracted much attention.In this thesis,a series of 4-aminoquinoline derivatives were constructed using one-pot method with simply and efficiently in the absence of transition metals.The first chapter introduces the research status of multi-component one-pot method.Then,the pharmacological activity,biological activity,photophysical properties of quinoline compounds and 4-aminoquinolines as well as the research process on their synthetic methods are introduced.In addition,the concept,pharmacological activity,biological activity of amide compounds as well as the research progress on their synthetic methods are briefly introduced.At the same time,the research significance and design ideas of this thesis are proposed.The second chapter developed a novel and efficient K₂S₂O₈-mediated acylation reaction of aromatic amines acetonitrile.The acetamide derivatives were synthesized through a multi-component one-pot method.The method uses aromatic amines,water and acetonitrile as reaction substrates and has the characteristics of simple operation and environmental friendliness.Through controlling contrasting experiments and previous work,it was found that the oxygen in the target product comes from water,and the reaction mechanism was studied.The third chapter reported a cyclization reaction without transition metal catalyzed oxidation with amines,benzenesulfonylacetonitrile and DMSO as substrates.A series of4-aminoquinoline derivatives were synthesized through a three-component one-pot method.Compared with the traditional method,this method also has good yield and substrate universality without using transition metal.Through the related control experiments,it is speculated that DMSO can not only be used as a solvent in the reaction,but also as a reactant to participate in the reaction,and a possible reaction mechanism is proposed.