Syntheses of 2-Spiroindoles and Pyrrolo[1,2-a]indoles. -C-alkylated products of 3-hydroxyindolecarboxylate (I) provide access to pyrroloindole structures [cf. (VII), (VIII)] as well as spirocyclic indole derivatives such as (VI), which represent indolic analogues of the spirocyclic piperidine alkalo
Syntheses of 2-spiroindoles and pyrrolof[1,2-a]indoles
✍ Scribed by B. Malapel-Andrieu; J.-Y. Mérour
- Publisher
- Journal of Heterocyclic Chemistry
- Year
- 1998
- Tongue
- English
- Weight
- 543 KB
- Volume
- 35
- Category
- Article
- ISSN
- 0022-152X
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✦ Synopsis
Abstract
C‐alkylated products obtained from methyl 3‐hydroxyindole‐2‐carboxylate afford either spiro compounds, such as an indolic analogue of nitramine, or tricyclic products with a pyrrolo[1,2‐a]indole framework. Di‐C‐alkylated derivatives give access to tetracyclic compounds.
📜 SIMILAR VOLUMES
## Abstract Heating of 1′‐(__N__‐substituted carbamoyl)methylspiro[2__H__‐1‐benzopyran‐2,2′‐[2__H__]indoles] with potassium hydroxide in ethanol yields diastereomeric 5a,13‐methano‐6__H__‐1,3‐benzoxazepino[3,2‐__a__]indole‐12‐carbox‐amides. Reduction of the latter with sodium borohydride affords 1,