Quinazolinone-to-Isoquinoline\nMetamorphosis by Ruthenium-Catalyzed\n[4+2] Annulation with Sulfoxonium Ylides

Molecular editing of quinazolinones to isoquinolines\nby a novel\nruthenium-catalyzed [4+2] annulation with sulfoxonium ylides has been\ndeveloped. The method permits the precise and rapid assembly of multisubstituted\naminoisoquinolines, a class of heterocycles that play a privileged\nrole in organic synthesis and pharmaceutical development. This new\ncatalytic process exhibits novel programmability, including directed\nC–H acetylation, nucleophilic cyclization, and alcoholysis.\nRemarkably, various 2-arylquinazolinones and sulfoxonium ylides could\nbe employed in excellent yields with broad functional group tolerance.\nThis heterocycle-to-heterocycle protocol is compatible with green\nchemistry using an EtOH solvent and releasing H<sub>2</sub>O and dimethyl\nsulfoxide as byproducts.