Furo- and thieno-fused 1,3-diazepine-4,6-diones

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. (C) 2013 Elsevier Ltd. All rights reserved.