## Abstract Phenylpropionamides acylated in the ortho position with aralkanecarboxylic acids were cyclised to give, after reduction, 1‐aralkyl‐tetrahydro‐2‐benzazepines.
1-Aralkylated Tetrahydro-2-benzazepines. Part III. Synthesis from β-tetralones
✍ Scribed by Daniel Berney; Karlheinz Schuh
- Publisher
- John Wiley and Sons
- Year
- 1976
- Tongue
- German
- Weight
- 626 KB
- Volume
- 59
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
1‐Benzyl‐tetrahydro‐2‐benzazepin‐3‐ones 4 were prepared by submitting the corresponding 1‐benzyl‐β‐tetralones 3 to the Schmidt reaction. On the other hand, the rearrangement of the tetralones 3 by the Beckmann procedure gave 1‐benzyl‐tetrahydro‐3‐benzazepin‐2‐ones 5. The syntheses of some hexahydrophenanthro‐azepines of types 10 and 15 are also described.
📜 SIMILAR VOLUMES
## Abstract 3‐(3,4‐Dimethoxyphenyl)‐propylamine was N‐acylated with aralkanecarboxylic acid chlorides. The resulting amides were subjected to __Bischler‐Napieralski__ ring closure to give the corresponding 1‐aralkyl‐dihydro‐2‐benzazepines. These were reduced to the title compounds.
Ring opening of indole functionalised methyleneaziridines (3a-c, 7) with alcohols in the presence of boron trifluoride etherate leads to the formation of 1,1-disubstituted tetrahydro-b-carbolines in moderate to good yields (37-83%).