抄録
Reactions of N-alkoxyquinolinium salts (1) with enamines of cyclohexanone (2) gave not the expected 2-(2-quinolyl) cyclohexanone but instead products of a novel tricyclic system (3) ; for example, 3-ethoxy-14-(2-quinolyl)-3-azabenzo[d]tricyclo[5, 3, 1, 12, 8]dodecan-13-ylidenemorpholinium iodide (3a) was obtained from N-ethoxyquinolinium iodide (1a) and the morpholine enamine (2a). The stereochemistry of 3a was finally established by X-ray diffraction study as C, but interesting informations supporting its structure were obtained by its chemical reactions which involed thermolysis to 2, 3'-biquinolyl (4a), stereoselective addition to the azomethinium moiety, alkaline hydrolysis to the corresponding ketone (7), pyrolytic elimination of ethylene oxide from some derivatives (5a, 7 and 8) and others. Spectral examinations of 3a and its transformed compounds also agreeded with its structure. The reaction mechanism was discussed.
