The mechanism of formation of 3H,9H-Pyrano[3,4-b]indol-3-ones from 3-indolalkanoic acids
✍ Scribed by Medio-Simon, Mercedes ;Erfanian-Abdoust, Houshang ;Pindur, Ulf
- Publisher
- John Wiley and Sons
- Year
- 1991
- Tongue
- English
- Weight
- 186 KB
- Volume
- 1991
- Category
- Article
- ISSN
- 0947-3440
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✦ Synopsis
Abstract
The mechanism of the formation of 1‐methyl‐3__H__,9__H__‐pyrano[3,4‐b]indol‐3‐one (4) from the corresponding 3‐indolacetic acid 1 is discussed. The suggested mechanism is substantiated by the isolation of a stable intermediate 2 and its transformations in the presence of acetic anhydride and/or Lewis acids.
📜 SIMILAR VOLUMES
## Abstract Pyrano[3,2‐__b__]indole derivatives **2**–**6** were synthesized in good yields from 1‐acetyl‐2‐benzylidene‐2,3‐dihydro‐1__H__‐indol‐3‐ones **8** and **13**–**15** by an intramolecular hetero‐__DielsAlder__ reaction. The structures of compounds **2a, 3a, 4, 5**, and **6** were unambigu