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, no.8, pp.1365-1370, 2010 (Journal Indexed in SCI) identifier identifier

  • Publication Type: Article / Article
  • Publication Date: 2010
  • Doi Number: 10.1055/s-0029-1218673
  • Title of Journal : SYNTHESIS-STUTTGART
  • Page Numbers: pp.1365-1370
  • Keywords: acyl azide, isocyanate, Curtius rearrangement, urethanes, benzodiazepinone, SELENIUM-ASSISTED CARBONYLATION, CYCLIC UREAS, BENZODIAZEPINE, CHEMISTRY, ACID

Abstract

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.