<scp>Copper‐Catalyzed</scp> Aerobic Oxidative Ring Expansion of Isatins: A Facile Entry to <scp>Isoquinolino‐Fused</scp> Quinazolinones
Dahan Wang, Fuhong Xiao, Feng Zhang, Huawen Huang, Guo‐Jun Deng
Abstract
A copper‐catalyzed aerobic oxidative ring expansion reaction of isatins with 1,2,3,4‐tetrahydroisoquinoline for the synthesis of tetracyclic 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. The capacity of the resultant 5 H ‐isoquinolino[1,2‐ b ]quinazolin‐8(6 H )‐one for a range of palladium‐catalyzed directing C—H activation has been further demonstrated, thus giving a broader access to diverse tetracyclic quinazolinones.
Topics & Concepts
ChemistryCatalysisRing (chemistry)Combinatorial chemistryOxidative phosphorylationCopperReaction conditionsMedicinal chemistryOrganic chemistryBiochemistryQuinazolinone synthesis and applicationsCatalytic C–H Functionalization MethodsSynthesis and Biological Evaluation