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New isomers of 4,1-benzothiazepines. The first evidence for the desmotropy of seven-membered heterocycles |
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| Authors: | Pé ter Csomó s,Lajos Fodor,Jari Sinkkonen,Gá bor Berná th |
| Affiliation: | a Institute of Pharmaceutical Chemistry, University of Szeged and Research Group for Heterocyclic Chemistry, Hungarian Academy of Sciences, H-6701, POB 427, Hungary b Central Laboratory, County Hospital, H-5701 Gyula, POB 46, Hungary c Department of Chemistry, University of Turku, FIN-20014 Turku, Finland |
| Abstract: | A novel procedure was developed for the preparation of 2,3-disubstituted 4,1-benzothiazepines, via the ring transformation of (2R∗,2aS∗)-2-chloro-2a-phenyl-2,2a-dihydro-2H,4H-azeto[1,2-a][3,1]benzothiazin-1-one (1) with sodium ethoxide in ethanol. The tautomeric products (R∗)-3-ethoxycarbonyl-2-phenyl-3,5-dihydro-4,1-benzothiazepine (4) and 3-ethoxycarbonyl-2-phenyl-1,5-dihydro-4,1-benzothiazepine (5) exhibit the rare phenomenon of desmotropy of the condensed seven-membered heterocycles. Surprisingly, these desmotropes could be separated by column chromatography. The products are unexpectedly stable in solution and their structures were proved by means of NMR and mass spectrometry. |
| Keywords: | Desmotropy 4,1-Benzothiazepine β-Lactam Ring transformation |
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