Diverting Reactive Intermediates Toward Unusual Chemistry: Unexpected Anthranil Products from Davis–Beirut Reaction

The discovery of a new variation on the Davis–Beirut reaction is described in which an atypical heterocyclic framework (the anthranil or benzo­[c]­isoxazole framework) is formed as the result of diversion of a key reactive intermediate away from its expected reactivitya potentially general approach to reaction design and development. Experimental and computational support for the proposed mechanism and origins of altered reactivity are described.