A SIMPLE METHOD FOR SYNTHESIZING 7-OXO-4-THIA-1-AZABICYCLO [3. 2. 0]-HEPTANE AND ITS 6-METHYL DERIVATIVES FROM ETHYL CYANOACETATE

Ethyl cyanoacetate (1a) or its methyl derivatives (1b and 1c) were treated with HCl/EtOH to give the corresponding imidates (2a-2c). Treatment of the latter compounds with cysteamine gave ethyl 2-thiazoline-2-acetate (3a-3c), which by reduction with sodium cyanoborohydride in HCl/MeOH gave the corre...

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Veröffentlicht in:	Chemical & pharmaceutical bulletin 1985/07/25, Vol.33(7), pp.3046-3049
Hauptverfasser:	Chiba, Takuo, Takahashi, Takumi, Sakaki, Junichi, Kaneko, Chikara
Format:	Artikel
Sprache:	eng
Schlagworte:	6, 6-dimethyl-4-thia-1-azabicyclo [3. 2. 0] heptan-7-one Chemistry Exact sciences and technology Heterocyclic compounds Heterocyclic compounds with n hetero atom and also o and/or s, se, te hetero atoms Organic chemistry Preparations and properties
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Beschreibung
Zusammenfassung:	Ethyl cyanoacetate (1a) or its methyl derivatives (1b and 1c) were treated with HCl/EtOH to give the corresponding imidates (2a-2c). Treatment of the latter compounds with cysteamine gave ethyl 2-thiazoline-2-acetate (3a-3c), which by reduction with sodium cyanoborohydride in HCl/MeOH gave the corresponding thiazolidines (4a-4c). Hydrolysis followed by β-lactam formation through the use of Mukaiyama-Ohno's reagent afforded 7-oxo-4-thia-1-azabicyclo [3. 2. 0] heptane (6a) and its methylated derivatives (6b and 6c).
ISSN:	0009-2363 1347-5223
DOI:	10.1248/cpb.33.3046