A simple and expedient method for the stepwise synthesis of 2-ethoxy-(4H)-3,1-benzoxazine-4-ones

A simple and practical route is described for the synthesis of 2-ethoxy-(4H)-3,1-benzoxazine-4-ones using the coupling reaction of anthranilic acid derivatives with diethyl dicarbonate following with fast cyclization of the carbamate adduct with a dehydrocyclization agent such as cyanuric chloride and N,N′-dicyclohexylcarbodiimide in PEG at room temperature. High yields of the products obtained under mild reaction conditions with simple work-up of the reaction mixture.