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

Ozer M. S., Koza G., ŞAHİN E., BALCI M.

TETRAHEDRON LETTERS, vol.54, no.48, pp.6553-6556, 2013 (SCI-Expanded) identifier identifier

  • Publication Type: Article / Article
  • Volume: 54 Issue: 48
  • Publication Date: 2013
  • Doi Number: 10.1016/j.tetlet.2013.09.103
  • Journal Name: TETRAHEDRON LETTERS
  • Journal Indexes: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Page Numbers: pp.6553-6556
  • Keywords: Benzodiazepinone, Furo-diazepinedione, Thieno-diazepinedione, Curtius rearrangement, ONE-POT SYNTHESIS, PRIVILEGED STRUCTURES, ORGANIC-SYNTHESIS, 1,4-BENZODIAZEPINE-2,5-DIONES, DERIVATIVES
  • Middle East Technical University Affiliated: Yes

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