Azabenzocycloheptenones. Part XVI. Amino-ketones of the tetrahydro-2-benzazepin-5-one series

Abstract

Attempts to remove the tosyl group from 1,2,3,4-tetrahydro-8-methoxy-2-tosyl-2-benzazepin-5-one and 1,2-di-hydro-8-methoxy-2-tosyl-2-benzazepin-5-one were unsuccessful. 2,3,4,5-Tetrahydro-8-methoxy-2-tosyl-1H-2-benzazepin-5-ol was detosylated by sodium in liquid ammonia and the product was converted into Nmethyl, Nacetyl, and Nbenzyloxycarbonyl derivatives, all of which were oxidised to the corresponding ketones. 2-Benzyl-oxycarbonyl-1,2,3,4-tetrahydro-8-methoxy-2-benzazepin-5-one was catalytically hydrogenolysed to 1,2,3,4-tetrahydro-8-methoxy-2-benzazepin-5-one. N-Alkyl andN-benzyl 1,2,3,4-tetrahydro-2-benzazepin-5-ones could not be obtained by Friedel–Crafts cyclisation of the corresponding amino-acids.