Angus McLean

Azabenzocycloheptenones. Part XVIII. Amines and amino-ketones of the tetrahydro-3-benzazepin-1-one series

2,3,4,5-Tetrahydro-3-benzazepin-1-one and its 3-benzyloxycarbonyl and 3-methyl derivatives have been synthesised from 2,3,4,5-tetrahydro-3-p-tolylsulphonyl-3-benzazepin-1-one. 2,3,4,5-Tetrahydro-7,8-dimethoxy-3-p-tolylsulphonyl-3-benzazepin-1-one was made by cyclisation of the corresponding glycine in polyphosphoric acid at 20° but all attempts to cyclise N-alkylglycines failed.

Azabenzocycloheptenones. Part XVII. Some substitution reactions in tetrahydro-1-benzazepin-5-ones

1,2,3,4-Tetrahydro-1-p-tolylsulphonyl-1-benzazepin-5-ones have been detosylated by two methods. N-Alkylation of 1,2,3,4-tetrahydro-1-benzazepin-5-one and 2,3-dihydro-1H-1-benzazepine with several reagents is reported. Substitution of the 4- and 5-positions of 1,2,3,4-tetrahydro-1-p-tolylsulphonyl-1-benzazepin-5-one has been studied and several transformation products are described. Dehydrogenation of 5,6-dihydrodibenz[b,e]-azepin-11-ones has been re-examined: the products are dibenz[b,c]azepin-11-ones.

Conversion of N-2-chloroallylanilines into 2-methylindoles

N-2-Chloroallylanilines give moderate yields of 2-methylindoles when heated with polyphosphoric acid at 100° possible mechanisms are discussed.