Furo- and thieno-fused 1,3-diazepine-4,6-diones |
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Authors: | Merve Sinem Ozer Gani Koza Ertan Sahin Metin Balci |
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Affiliation: | 1. Department of Chemistry, Middle East Technical University, 06800 Ankara, Turkey;2. Department of Chemistry, Ahi Evran University, 40100 K?r?ehir, Turkey;3. Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey |
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Abstract: | We report the first preparation of furo- and thieno-fused 1,3-diazepine-4,6-dione derivatives starting from ethyl 2-(2-methoxy-2-oxoethyl)-3-furancarboxylate and -thiophencarboxylate. The ester functionalities connected to the hetero-ring were converted regiospecifically into the desired amides. The ester groups attached to the methylene unit were converted into isocyanates via Curtius rearrangement. The ring-closure reaction was performed in the presence of lithium bis(trimethylsilyl)amide at room temperature to give furo- and thieno-fused diazepinone derivatives. |
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Keywords: | Benzodiazepinone Furo-diazepinedione Thieno-diazepinedione Curtius rearrangement |
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