2,6-Piperidinediones, I. Synthesis of the Racemates and the Enantiomers of 3,3-Disubstituted 2,6-Piperidinediones
β Scribed by Joachim Knabe; Dirk Reischig
- Publisher
- John Wiley and Sons
- Year
- 1984
- Tongue
- English
- Weight
- 561 KB
- Volume
- 317
- Category
- Article
- ISSN
- 0365-6233
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π SIMILAR VOLUMES
Among the racemic 2.6-piperidinediones 1-6, compound 6 has the highest anesthetic activity. The enantiomers of 1, 2 , 4 and 5 possess different anesthetic potencies depending on the nature of the aliphatic side chain. The S(-)-enantiomen of the piperidinediones 2, 3 and 5 cause initial CNS stimulati
The PPA induced Fischer indolization of 4-acetonyl-2,6-piperidinediones 4 takes place both at the methylene and the methyl carbons, although the latter regioisomer (3) undergoes a further cyclization of the imide moiety upon the indole 3position followed by ring-opening of the resulting intermediate
In a short sequence, 5-vinyloxazolidin-2-ones were converted into the 3,6-disubstituted 3,6-dihydropyridin-2-ones via Pd-catalysed carbonylation and enolate alkylation with high diastereoselectivity. Alkylation of 6-substituted N-methylpyridin-2ones gives stereoselectively the 3,6-anti diastereoisom