Study On The Reaction Of 2-vinylarylamine With Acetophenone / Chloroform To Synthesize Quinoline Compounds

Compounds containing quinoline rings are one of the representatives nitrogen-containing aromatic heterocyclic compounds.Due to its unique structure,it is often used as a base in organic synthesis and as a pharmaceutical intermediate.Quinoline compounds are widely present in natural products and synthetic products,it has important applications in anti-tuberculosis,anti-cancer,anti-psychotic drugs,anti-inflammatory,and anti-HIV.Therefore,the synthesis of quinoline compounds is of great significance.In this thesis,through investigating the progress in the synthesis of quinoline compounds,we designed and explored the reaction of vinyl arylamine with acetophenone to synthesize 2-acyl quinoline promoted by iodine and studied the alkali-promoted vinyl aromatic amine and tris chloromethane to synthesis quinoline compounds.The work during the master's degree is as follows:1.The research progress in the synthesis of quinoline compounds in recent years is summarized.2.We used iodine as the oxidant and DMSO as the solvent.At 80 ^oC,2-?1-arylvinyl?aniline and acetophenone were reacted to prepare a series of2-acylquinolines.The reaction raw material is simple to prepare,simple and convenient to operate,no metal is required,the target product can be obtained with medium to excellent yield,and the substrate also has good adaptability.3.NaOH was used as a base,chloroform was used as an reactant,and dioxane was used as a solvent,At 80°C,the cyclization of vinyl aromatic amine was achieved.This reaction uses chloroform to react with strong base to form dichlorocarbene,and then reacts with vinyl aromatic amine to obtain aromatic isonitrile,subsequently,ring closure under proton conditions to synthesize a series of important quinoline products.Besides,the reaction does not require metals,mild conditions,simple operation.The structure of the above target product was confirmed by ¹H NMR,¹³C NMR and HRMS.