Study On The Selective Construction Of Quinolines And Azepines By Copper-Catalyzed N-β-C(sp~3)-H Functionalization

Nitrogen-containing heterocyclic compounds are not only important organic synthesis intermediates,but also the core skeleton of many drugs,functional materials and natural products.Among them,six-membered quinolines and seven-membered azepines are widely present in drug molecules.These drugs have good biological activity in anti-depressant,anti-cancer,and anti-malaria,etc.,and also have high medical value.Therefore,the search for more efficient and economical synthetic strategies to construct quinoline and azepine compounds has always been one of the important topics in field of organic synthesis.In recent years,with the significant progress of transition metal-catalyzed C（sp³）-H functionalization in the field of synthetic chemistry,researchers have used this method to develop some new strategies for the construction of quinoline and azepine compounds,which generally have the advantages of well yield and high atomic economy,but most of them require the catalysis of precious metals.Based on the review and analysis of relevant literature,methods were developed for the selective construction of quinoline and azepine compounds via copper catalyzes N-β-C（sp³）-H functionalization.The main research content of this paper includes the following three chapters:The first chapter reviews the research progress in the construction of quinoline and azepine compounds in recent years.The second chapter developed a new means of copper-catalyzed N-β-C（sp³）-H functionalization to construct quinoline compounds.This reaction can quickly and efficiently construct quinoline compounds via the breaking of N-β-C（sp³）-H bond and the formation of C-O,C-N,and C-C bonds,which involve 1-aryl-2-（（2-（arylethynyl）aryl）amino）Propane-1-one in the presence of Cu（OAc）₂ as catalyst and oxidant in DMSO.This strategy has the advantages of stable substrate,simple operation and low cost.The third chapter based on the synthesis of quinoline compounds,azepine derivatives were selectively synthesized by changing the reaction conditions.This method may simply and efficiently construct a series of azepine derivatives though N-β-C（sp³）-H functionalization,which uses1-aryl-2-（（2-（arylethynyl）aryl）amino）propane-1-one in the presence of Cu（OAc）₂ as catalyst and oxidant in toluene.