Construction And Transformation Of 2,3-Dihydro-4-quinolinone Catalyzed By Bi?OTf?₃

The quinolinone moiety is widely present in natural products,and compounds containing such unit not only have significant biological activities,but also are used as organic synthesis intermediates of great value.But it is still a very challenging task to build this unit easily.Based on the previous research results,this thesis carried out the construct-ion and transformation of 2,3-dihydro-4-quinolinone compounds using triflate as a catalyst.Firstly,we successfully cascaded the Meyer-Schuster reaction/intramolecular hydroamination/halogenation reaction to explore a one-pot synthesis of 3-halo-2,3-dihydro-4-quinolinones,which has a high yield and a wide range of substrate applications.Subsequently,in a further attempt,we successfully converted the halogen and carbonyl groups in the 3-halo-2,3-dihydro-4-quinolinone compound into a thiazole ring,and explored a one-pot synthesis of 4,5-dihydrothiazolo[5,4-c]quinolin-2-amine compounds.This is an efficient and simple synthesis method,of which neither the route nor the product has been reported.