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Synthesis 2010(8): 1365-1370  
DOI: 10.1055/s-0029-1218673
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

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

Cagatay Dengiza, Sevil Özcana,b, Ertan Şahinc, Metin Balci*a
a Department of Chemistry, Middle East Technical University, 06531 Ankara, Turkey
Fax: +90(312)2103200; e-Mail: mbalci@metu.edu.tr;
b Department of Chemistry, Abant Izzet Baysal University, 14280 Bolu, Turkey
c Department of Chemistry, Atatürk University, 25240 Erzurum, Turkey
e-Mail: ertan@atauni.edu.tr;
Further Information

Publication History

Received 13 December 2009
Publication Date:
11 February 2010 (online)

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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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