The authors have studied the reduction of naphtostyril (I, R = H) and of the corresponding 4‐methoxy derivative IIIa by amalgamated sodium in water to 2a,3,4,5‐tetrahydronaphtostyril (II, R = H) and its 4‐keto derivative IV, respectively.
Umwandlung von 2a, 3, 4, 5-Tetrahydronaphtostyril in 1, 3, 4, 5-Tetrahydrobenz[cd]indol. Benz[cd]indol-Reihe
✍ Scribed by C. A. Grob; W. Meier; E. Renk
- Publisher
- John Wiley and Sons
- Year
- 1961
- Tongue
- German
- Weight
- 508 KB
- Volume
- 44
- Category
- Article
- ISSN
- 0018-019X
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✦ Synopsis
Three methods for converting the oxindole ring of 2a,3,4,5‐tetrahydronaphtostyril (Ia) into the indole ring of 1,3,4,5‐tetrahydrobenz[cd]indole (I1 a) are described.
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The synthesis of 5‐keto‐2a,3,4,5‐tetrahydronaphtostyril (3) via 4‐nitro‐indanone is described.
## Abstract Es wird eine praktische Synthese des 5‐Keto‐1,3,4,5‐tetrahydrobenz(cd)indols beschrieben. Die Hauptmerkmale dieser Synthese sind: Die Überführung von 1‐Methoxy‐5‐acetamino‐naphtalin in 5‐Oxy‐benz(cd)indolin in drei Stufen; Die Isomerisierung von 5‐Oxy‐benz(cd)indolin zu 5‐Keto‐1,3,4,5
## Abstract In contrast to the facile isomerisation of 5‐hydroxy‐benz(cd)‐indoline (Ia) to 5‐keto‐1, 3, 4, 5‐tetrahydro‐benz(cd)indole (II) reported earlier, its N‐acetyl derivative Ib is not isomerised to the N‐acetylated ketone III in the presence of a palladium catalyst.