Abstract
When 2-(2-quinolyl) cyclohexanone oxine (Ia) was treated with tosylchloride under basic conditions of the Beckmann rearrangement, a new cyclization reaction took place to produce a new compound, 7, 8, 9, 10-tetrahydro-11a-azabenzo[a]carbazole (IIa) in almost quantitative yields. On the other hand, the normal Beckmann rearrangement proceeded when Ia was heated with conc. sulfuric acid to give the lactam compound, 2-oxo-7-(2-quinolyl) cyclohexamethyleneimine (IV) in an extremely high yield. The corresponding oximes of lepidine (Ib) and pyridine (XIV) gave also similar results. The structures of the products were confirmed by chemical methods and by the ultraviolet, infrared and nuclear magnetic resonance spectral examinations. The mechanisms of the above reactions are then discussed.
