A series of new 4-methoxybenzylaminoacetonitriles has been prepared and characterised. These have been cyclised with concentrated sulphuric acid and a new non-classical mechanism is postulated. Depending on the nature and position of the substituent groups on the nitrile the following classes of compound have been prepared: 4-oxo-tetrahydroisoquinolines, 3-imidazolines, 3,3-disubstituted tetrahydroisoquinolines, N-substituted tetrahydroisoquinolines, 2-benzazepines. The mechanism postulated satisfactorily explains the formation of all the above classes of compound and also the formation of certain 3,3-disubstituted-4-oxo-tetrahydroisoquinolines previously reported. Structural assignments have been made by means of elemental analysis and infrared spectroscopy; extensive use has been made of nuclear magnetic resonance and mass spectroscopy. Several new compounds have been tested for biological activity.
|Date of Award||1976|