Studies on quinones. Part 25. Synthetic approaches to 6,9-dioxygenated-benzazepinones

The Schmidt and Beckmann rearrangement of 3,4-dihydro-4,4-dimethyl-1(2H)-naphthalenones bearing oxygenated groups at the 5,8-positions, and some of their oximes are reported. Depending upon the structure of the substrates and the reaction conditions 4,5-dihydro-3H-naphth1,8-cd]isoxazol, benzazepin-2-one and 5,6-dihydro-7H-tetrazolo1,5-a]2]benzazepine derivatives were generated.