Secondary Interactions Arrest the Hemiaminal Intermediate To Invert the Modus Operandi of Schiff Base Reaction: A Route to Benzoxazinones.

Discovered by Hugo Schiff, condensation between amine and aldehyde represents one of the most ubiquitous reactions in chemistry. This classical reaction is widely used to manufacture pharmaceuticals and fine chemicals. However, the rapid and reversible formation of Schiff base prohibits formation of alternative products, of which benzoxazinones are an important class.