Microwave-Assisted Palladium-Catalyzed Reductive Cyclization/Ring-Opening/Aromatization Cascade of Oxazolidines to Isoquinolines

An efficient palladium-catalyzed reaction of N-propargyl oxazolidines for the construction of 4-substituted isoquinolines under microwave irradiation is developed. This transformation proceeds through a sequential palladium-catalyzed reductive cyclization/ring-opening/aromatization cascade via C-O and C-N bond cleavages of the oxazolidine ring. The practical value of this method has also been explored by conducting a millimole-scale reaction, as well as by transforming the isoquinoline into a key intermediate for the synthesis of a lamellarin analogue.

Automated summary

An efficient palladium-catalyzed reaction under microwave irradiation has been developed for the construction of 4-substituted isoquinolines through a sequential palladium-catalyzed reductive cyclization/ring-opening/aromatization cascade. The practical value of this method was demonstrated by conducting millimole-scale reactions and transforming the isoquinoline into a key intermediate for the synthesis of a lamellarin analogue.