Condensation of O-phenylhydroxylamine with 1H-2,3,4,5,6,7-hexahydroazepine-2,4-dione in alcoholic hydrogen chloride solution gave 1-oxo-1H-2,3,4,5-tetrahydrobenzofuro[3,2-c]-azepine, while a similar condensation with 6,6-dimethyl-1H-2,3,4,5,6,7-hexahydroazepine-2,4-dione gave a mixture of 4,4-dimethyl-1H-2,3,4,5-tetrahydrobenzofuro[3,2-c]azepine and 2-oxo-3-(3′,3′-dimethyl-5′-pyrrolidylidene)benzofuran. Tetrahydrobenzofuroazepines were also synthesized by Beckmann rearrangement of oximes of 1-oxo-1,2,3,4-tetrahydrobenzofuran and 3,3-dimethyl-1-oxo-1,2,3,4-tetrahydrodibenzofuran, which were obtained in turn by condensation of O-phenylhydroxylamine with dihydroresorcinol and dimedone.