Synthesis of Phenyl- and Benzyl-Substituted Pyrrolidines and of a Piperidine by Intramolecular C-Alkylation. Synthons for tricyclic skeletons
✍ Scribed by Roland Achini
- Publisher
- John Wiley and Sons
- Year
- 1981
- Tongue
- German
- Weight
- 994 KB
- Volume
- 64
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Abstract
The construction of new or novelly functionalized annulated and bridged tricylic compounds by two consecutive C,C‐bond formations (a and b in la, Scheme 1) is described. In a first step, chloroalkyl‐substituted aminonitriles yielded pyrrolidines 8, 15a, 15b, 23, 25 and piperidine 18 by carbanionic ring closure (Schemes 5, 6, 7 and 8). Subsequent Friedel‐Crafts cyclization transformed the β‐aminonitriles 8, 15a, 15b, and 18 either directly or via their carboxylic acid derivatives to the indeno [1, 2‐c]pyrrole, 2, 5‐methano‐3‐benzazocine, benz [f]isoindoline and 1, 4‐ethano‐2‐benzazapine skeletons 11, 16a, 16b and 21, respectively (Schemes 5, 6 and 7). By classical ring expansion reactions the pyrrolo [3, 4‐c]isoquinoline and benzopyrano‐[3, 4‐c]pyrrole skeletons 28 resp. 31 were obtained from 11 (Scheme 9).