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

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Ozer M. S., Koza G., Şahin E., Balci M.

TETRAHEDRON LETTERS, cilt.54, ss.6553-6556, 2013 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Cilt numarası: 54
  • Basım Tarihi: 2013
  • Doi Numarası: 10.1016/j.tetlet.2013.09.103
  • Dergi Adı: TETRAHEDRON LETTERS
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.6553-6556
  • Anahtar Kelimeler: Benzodiazepinone, Furo-diazepinedione, Thieno-diazepinedione, Curtius rearrangement, ONE-POT SYNTHESIS, PRIVILEGED STRUCTURES, ORGANIC-SYNTHESIS, 1,4-BENZODIAZEPINE-2,5-DIONES, DERIVATIVES
  • Bursa Uludağ Üniversitesi Adresli: Hayır

Özet

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.