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Synthesis 2010(8): 1365-1370
DOI: 10.1055/s-0029-1218673
DOI: 10.1055/s-0029-1218673
PAPER
© Georg Thieme Verlag
Stuttgart ˙ New YorkNew Synthetic Methodology for Construction of the 1,3,4,5-Tetrahydro-2H-1,3-benzodiazepin-2-one Skeleton
Weitere Informationen
Received
13 December 2009
Publikationsdatum:
11. Februar 2010 (online)
Publikationsverlauf
Publikationsdatum:
11. Februar 2010 (online)

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.
Key words
acyl azide - isocyanate - Curtius rearrangement - urethanes - benzodiazepinone
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