Rh-Catalyzed C-H Addition of Quinazolines to Alkenes

Significance

An elegant direct Rh-catalyzed addition of unactivated acyclic and cyclic olefins to dihydroquinazolines A and quinazoline D has been developed. The reaction proceeds via Rh-promoted C-H activation followed by alkene addition ­under mild conditions to give products B and C in good to excellent yields. An intramolecular version, E → F, was also reported and the method was applied to the synthesis of Vasicoline (6 steps, 8% overall yield), an alkaloid isolated from Adhatoda vasica, which exhibits antimalarial, antiinflammatory, and antitumor activity.