The Reaction Of Phenylacetone Or Phenylacetylene,Aniline And Dimethyl Sulfoxide To Synthesize Quinoline Compounds

Quinoline compounds are very important in organic chemistry and have remarkable drug and biological activity.Therefore,the synthetic method of this compound has received wide attention from researchers.For example,2-aryl quinoline stents are used in their respective drugs,such as p-selectin antagonists,antimalarial drugs and anti-tumor activity.As a result,the researchers have made a great contribution,has made important scientific research achievements,however,most of these methods have some limitations,such as synthetic instead of quinoline production rate is not high,product separation,harsh reaction conditions,the applicability of the substrate is poor,limit the application of this reaction in organic chemistry.Therefore,based on the concept of high efficiency and atomic economy,it is necessary to develop a new method of synthesis of quinoline compounds from commercial and user friendly materials.In this thesis,we investigated acetophenone or phenyl acetylene this paper around acetophenone or phenyl acetylene,aniline and dimethyl sulfoxide three molecular reaction synthesis of quinoline compounds were studied systematically,the main contents are as follows:(1)The progress of the synthesis of quinoline and its derivatives is reviewed,and the significance,purpose and main content of this paper are described.(2)A systematic study was conducted on the reaction of the ketone compounds catalyzed by dihydrochloride catalyzing the conversion of quinoline compounds.Aniline and acetophenone as the substrate for simulation,the reaction conditions for the selection and optimization,the optimum reaction conditions were got: acetophenone(0.5 tendency),benzyl ammonium(1.5 equiv),two water copper chloride(10 mol %),dimethyl sulfoxide(2.5 mL),120 °C,24 h,oxygen(1 atm).Then,the application scope of the substrate was investigated in the optimal condition.The results showed that both acetone and aniline had good compatibility.Then the reaction mechanism was explored,and the possible reaction mechanism was proposed according to the experimental results and related literature reports.(4)The reaction of the conversion of quinoline compounds by copper catalyzed by dihydrate was systematically studied.Aniline and phenyl acetylene substrates for simulation,the reaction conditions for the selection and optimization,the optimum reaction conditions: acetophenone(0.5 tendency),benzyl ammonium(1.5 equiv),two water copper chloride(10 mol %),dimethyl sulfoxide(2.5 mL),120 °C,24 h,oxygen(1 atm).Then,the application scope of the substrate was investigated in the optimal condition.The results show that both phenylacetylene and aniline substrates have good compatibility.