Electrochemical Oxidation Functionalization Of Quinazoline And Quinoline N-oxide Derivatives

Nearly two hundred years,organic electrochemical synthesis from theory into reality gradually,in the laboratory to industrialization,especially in nearly a decade of chemical workers through theoretical guidance research,enrich the theory,through research gradually systematic organic electrochemistry are summarized as a kind of than traditional organic synthesis methods have advantages.Quinoline and quinazoline ring,as a common nitrogen-containing heterocyclic ring,have been widely used in organic synthesis and biological medicine.In this paper,the advantages of electrochemical synthesis and the use of electrochemical methods in quinazoline N-oxide and quinoline N-oxide nitrogen heterocyclic activated C(SP~2)-H bond to achieve functional group research.The research mainly includes the following three parts:1.A simple and efficient reaction for direct conversion of quinazoline N-oxide to quinazolinone under electrochemical conditions was developed.A variety of quinazolinone compounds,which exist widely in natural products and drug molecules,were synthesized by this reaction.The reaction conditions of this transformation are simple and easy to operate,and there is no need of additional oxidant and transition metal catalyst.Through mechanism verification experiments we found that water is extremely important in the reaction.And successfully realized the gram scale experiment.2.A simple and efficient reaction was developed for the C-H/N-H coupling of quinazoline N-oxide with pyrazole or triazole under electrochemical conditions.A series of pyrazole or triazole-substituted quinazolines were synthesized by electrochemical method using pyrazole or triazole-substituted quinazoline-N-oxides in a three-nosed integrated cell.At the same time,we have successfully realized the gram scale scale experiment,which proves that this research has the initial value of industrial production.2.A simple and efficient coupling reaction of quinoline N-oxide with pyrazole or triazole multi-site C-H/N-H was developed under electrochemical conditions.The reaction was carried out in a three-neck cell.A series of pyrazole or triazole substituted quinoline N-oxide derivatives were synthesized by electrochemical method using pyrazole or triazole-substituted quinoline N-oxide derivatives.