New Synthetic Methodology for Construction of the 1,3,4,5-Tetrahydro-2H-1,3-benzodiazepin-2-one Skeleton

DENGİZ Ç., OZCAN S., ŞAHİN E., Balci M.

SYNTHESIS-STUTTGART, sa.8, ss.1365-1370, 2010 (SCI-Expanded) identifier identifier

  • Yayın Türü: Makale / Tam Makale
  • Basım Tarihi: 2010
  • Doi Numarası: 10.1055/s-0029-1218673
  • Dergi Adı: SYNTHESIS-STUTTGART
  • Derginin Tarandığı İndeksler: Science Citation Index Expanded (SCI-EXPANDED), Scopus
  • Sayfa Sayıları: ss.1365-1370
  • Anahtar Kelimeler: acyl azide, isocyanate, Curtius rearrangement, urethanes, benzodiazepinone, SELENIUM-ASSISTED CARBONYLATION, CYCLIC UREAS, BENZODIAZEPINE, CHEMISTRY, ACID
  • Orta Doğu Teknik Üniversitesi Adresli: Evet

Özet

We hereby report a new synthetic methodology for construction of the 1,3,4,5-tetrahydro-2H-1,3-benzodiazepin-2-one skeleton. 2-(2-Carboxyethyl)benzoic acid was converted into the corresponding bis(acyl azide). Curtius rearrangement of the diazide followed by reaction with alcohols provided diurethane derivatives. Ring-closure reaction of the diurethanes with base resulted in formation of the 1,3-benzodiazepin-2-one skeleton.