Rh(III)-Catalyzed Tandem Reaction Access to (Quinazolin-2-yl)methanone Derivatives from 2,1-Benzisoxazoles and α-Azido Ketones
Shan Liu, An‐Jing Wang, Min Li, Jing Zhang, Guodong Yin, Wen‐Ming Shu, Weichu Yu
Abstract
A Rh(III)-catalyzed tandem reaction for the synthesis of (quinazolin-2-yl)methanone derivatives has been explored from 2,1-benzisoxazoles and α-azido ketones. The transformation involves Rh(III)-catalyzed denitrogenation of α-azido ketones, aza-[4 + 2] cycloaddition, ring opening, and dehydration aromatization processes. Notably, the aza-[4 + 2] cycloaddition of an imine rhodium complex intermediate with 2,1-benzisoxazoles is the key to this reaction.
Topics & Concepts
ChemistryCycloadditionAromatizationCatalysisRing (chemistry)ImineRhodiumMedicinal chemistryTandemCombinatorial chemistryStereochemistryOrganic chemistryMaterials scienceComposite materialQuinazolinone synthesis and applicationsSynthesis and Biological EvaluationAsymmetric Hydrogenation and Catalysis