Rhodium-catalyzed Ortho C-H Bond Activation Of 2-aryl Quinazolinone Derivatives

In recent years,transition metal-catalyzed C-H bond activation reaction has developed rapidly.The rhodium,which has high reactivity,regional selectivity and extensiveness,has become a new attractive catalyst.Thus a large number of works on C-H bond activation reaction have been reported.On the other hand,as a class of important heteroaromatic compounds,quinazolinones are widely present in various important bioactive natural products.It is known that 4(3H)-quinazolinone derivatives have been great applications in the field of biomedicine with its useful biological activities.Therefore,it is of great value to smuggle diverse functional groups into the mother structural scaffold of quinazolinones.In this paper,base on the research on alkenylation reaction and cyclopropanol compounds in recent years and the experience of our group's in quinazolinone derivatives research,we intend to realize regioselecctively functional of2-arylquinazolinone with developing two strategies of the rhodium catalysis.In the first chapter,the recently progress of C-H bond activation reaction catalyzed by transition metal rhodium,alkenylation reaction of cyclopropanol compounds,and the quinazolinone derivatives are discussed.In the second chapter,we have developed an efficient method for vinylation of2-arylquinazolin-4-ones with vinyl acetate.Under the rhodium-catalyzed conditions,proceed with C-H,N-H bond activated and alkenylation cyclization,it synthesize selectively isoquinolino[1,2-b]quinazolin-8-one derivatives and12-methyl-12H-isoindolo[1,2-b]quinazolin-10(12H)-one derivatives.In the third chapter,we have developed an efficient method for the selective alkylation of 2-arylquinazolin-4(3H)-ones with cyclopropanols at room temperature.Under the rhodium-catalyzed conditions,the reactions of 2-arylquinazolin-4(3H)-ones and cyclopropanols,which proceed a series reaction of C-H bond activated and alkylation,gave the desired product of2-(2-(3-oxobutyl)phenyl)quinazolin-4(3H)-ones.