Chiral 3-hydroxyoxindoles are biologically important molecular motifs which are frequently present in natural products and artificial compounds.Herein,we report an ultraviolet light-driven asymmetric vinylogous aldol reaction between versatile isatins and 2-alkylbenzophenones.Under mild conditions.
Shixuan CaoJiatian LiTaishan YanJie HanZhengjie He
A copper-catalyzed aerobic oxidative ring expansion reaction of isatins with 1,2,3,4-tetrahydroisoquinoline for the synthesis of tetra-cyclic quinazolinones has been developed.This reaction is performed smoothly under simple conditions to give the corresponding products in moderate to good yields with good functional group tolerance.
Dahan WangFuhong XiaoFeng ZhangHuawen HuangGuo-Jun Deng
Described here is the first example of Cu(0)-catalyzed intramolecular decarbonylative rearrangements of readily available N-aryl isatins assisted by solvent dimethyl sulfoxide(DMSO)under air atmosphere and additive-free conditions leading to various biologically important acridones in good to excellent yields.This novel transformation is proposed to go through a sequential DMSO-aided Cu insertion into the amide C-N bond,CO extrusion,Cu migration,reductive elimination and DMSO-aided proton migration processes,involving multiple types of bond cleavage and formation in a single chemical step.
The first HFIP-promoted catalyst-free cascade reactions for the synthesis of biologically relevant 3,3-di(indolyl)indolin-2-ones(27 examples,up to 98% yield) from readily available indoles and isatin derivatives are described.This protocol shows well tolerance of different functional groups and features mild reaction conditions such as short reaction time(~1 h),no usage of catalyst,easy operation and product isolation.Of particular intere st is the formation of two C-C bonds and one all-carbon quaternary center.This protocol could serve as an alternative strategy to synthesize biologically important 3,3-di(indolyl)indolin-2-ones for biological testing.
Xiaohan YuanShuai WangJialing ChengBin YuHong-Min Liu
