The Design,synthesis And Structural Characterization Of Novel Quinoline Derivatives

Heterocyclic compounds are the largest number of organic compounds,and also a very important class of compounds.Heterocyclic heterocyclic structures and their derivatives have an active physiological activity in medicine and pesticides.With the progress of science technology and the development of society,the emergence of new diseases which has been a hot research topic to develop a new type of drug with broad spectrum and can cure many diseases.Heterocyclic structures and their derivatives have an active physiological activity in medicine and pesticides.Quinoline and its derivatives are important intermediates of organic drugs,which are widely used in the fields of clinical,agricultural drug screening,chemical analysis,dye industry and so on.Meanwhile,quinoline also exists in natural products such as antitumor drug camptothecin analogs.In recent years,more and more polysubstituted quinoline derivatives have been synthesized and shown more physiological activities.Therefore,it’s very important to study the synthesis of new polysubstituted quinoline derivatives for pharmaceutical research.Considering the principle of combination of drug design,in the experiment,we put the phenyl piperazine,triazole ring into the 2position of the quinoline ring,then synthesized a series of new 2,3-disubstituted quinoline derivatives,which might have potential biological activity,and also could provide lead compounds for organic synthesis and screening of drugs.The main subject of our study is to introduce 1,2,4-triazole and phenyl piperazine as substituents into 2 position of the quinoline molecule,obtained the key intermediates 2-(1,2,4-triazole-1-yl)-6-methyl-3-quiniline carboxaldehyde and2-(4-phenyl piperazin-1-yl)-quinolin-3-carbaldehyde,and exploited the carbaldehyde group of 3 position,three series of novel and 38 potentially biologically active2,3-disubstituted quinoline derivatives were synthesized.The structures of the obtained target compounds were elucidated by MS,IR,1H NMR,and elemental analyses.This paper is divided into two parts:The first part is the literature review,mainly introduces the status of quinoline,triazole,piperazine and pharmacological activities,the synthesis method of these drugs.The second part is the experimental part.This part mainly introduced the 2-chloro-2-3-formaldehyde as raw materials,2-position chlorine of the quinoline molecule substituted by 1H-1,2,4-triazole or phenyl piperazine,then 3 position aldehyde(1)with benzene-1,2-diamine reaction to produce benzimidazole,and then reaction with 2-(chloromethyl)-5-phenyl-1,3,4-oxadiazoleheterocyclic,then a series of heterocyclic compounds containing benzene imidazole,oxadiazoles,piperazine was synthesized;(2)oxidized to quinolinic acid methyl ester,hydrazine solution of hydrazine in CS2/KOH generates glucosinolates potassium,then important intermediate quinoline amine sulphur was synthesized,finally after a series of reactions to the target product quinoline derivatives containing triazole,triazine;(3)reaction with substitution acetophenone,chalcone and amino acid can be used to produce the pyrazoline,and finally,a heterocyclic compound containing pyrazole and thiazole can be generated.