A mild base-promoted three-component deconstructive functionalization of exocyclic 1,3-dicarbonyls with aryl diazonium tetrafluoroborates in the presence of alcohols is reported,enabling direct ring-opening of unstrai...A mild base-promoted three-component deconstructive functionalization of exocyclic 1,3-dicarbonyls with aryl diazonium tetrafluoroborates in the presence of alcohols is reported,enabling direct ring-opening of unstrained cyclic ring systems to produce six types of skeletally diverse hydrazonylated 1,n-diesters(e.g.,1,6-,1,7-1,8-,and 1,9-diesters)and 1,n-ketoesters(e.g.,1,6-and 1,7-ketoesters)with good yields,and the latter demonstrated complete(E)-selectivity.The methodology has the potential to be widely used throughout organic synthesis due to the use of easily accessible substrates with different substitution patterns,such as exocyclic 1,3-carbonyls and aryl diazonium tetrafluoroborates,and mild reaction conditions.Preliminary biological evaluation of some compounds,namely their inhibitory effect on human lung cancer cell MSTO-211H,was conducted.The results showed that compounds 3c and 3w exhibited significant inhibitory effects.展开更多
文摘A mild base-promoted three-component deconstructive functionalization of exocyclic 1,3-dicarbonyls with aryl diazonium tetrafluoroborates in the presence of alcohols is reported,enabling direct ring-opening of unstrained cyclic ring systems to produce six types of skeletally diverse hydrazonylated 1,n-diesters(e.g.,1,6-,1,7-1,8-,and 1,9-diesters)and 1,n-ketoesters(e.g.,1,6-and 1,7-ketoesters)with good yields,and the latter demonstrated complete(E)-selectivity.The methodology has the potential to be widely used throughout organic synthesis due to the use of easily accessible substrates with different substitution patterns,such as exocyclic 1,3-carbonyls and aryl diazonium tetrafluoroborates,and mild reaction conditions.Preliminary biological evaluation of some compounds,namely their inhibitory effect on human lung cancer cell MSTO-211H,was conducted.The results showed that compounds 3c and 3w exhibited significant inhibitory effects.
