Tetrahydropyridoazepines and tetrahydropyridoazepinones from the corresponding dihydroquinolones

The p ‐toluenesulfonate of 7,8‐dihydro‐5(6 H )quinoloneoxime( 3 ) was subjected of a Beckmann rearràngement. The resulting 2,3,4,5‐tetrahydro‐1 H ‐pyrido[3,2‐ b ]azepin‐2‐one ( 4 ) was reduced with lithium aluminum hydride affording 2,3,4,5‐tetrahydro‐1 H ‐pyrido[3,2‐ b ] azepine ( 5 ). 5,6‐l)ihydro‐8(7 H )quinolone ( 7 ), obtained by oxidation of 5,6,7,8‐tetrahydro‐8‐quinolinol ( 6 ), was converted into the p ‐toluenesulfonate of 5,6‐dihydro‐8(7 H )quinolone oxitne ( 9 ). Similarly the latter compound could be rearranged into 2,3,4,5‐letrahydro‐1 H ‐pyrido [2,3‐ b ] azepin‐2‐one ( 10 ) which on reduction produced 2,3,4,5‐tetrahydro‐1 H ‐pyrido [2,3‐ b ] azepine ( 11 ).