The cyclisation of some substituted benzylaminoacetonitriles.

Abstract

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
Original language	English
Awarding Institution	University of Bath