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Synthesis of 6-alkyl analogues of the 1-azabicyclo[4.3.0]nonan-2-one system by a strategy of geminal acylation and Beckmann rearrangement


Book ID
120327481
Publisher
Royal Society of Chemistry
Year
2001
Weight
257 KB
Volume
2
Category
Article
ISSN
1472-7781

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Reactions of 4-Oxoalkanoic Acids, 4. Syn
✍ Wedler, Christine ;Schick, Hans ;Scharfenberg-Pfeiffer, Doris ;Reck, GΓΌnter πŸ“‚ Article πŸ“… 1992 πŸ› John Wiley and Sons 🌐 English βš– 432 KB

## Abstract Ethyl 4‐oxoalkanoates 1 react at ambient temperature in dry methanol in the presence of molecular sieve 3 Γ… in almost quantitative yield with 3‐aminopropanol and 2‐aminoethanol to form the bicyclic lactams __rac__‐2 and __rac__‐3, respectively. Surprisingly, the (Β±)‐5‐alkyl‐4‐oxa‐1‐azab