Benzodiazepines peptidomimetics design

Ring expansion of homophthalic anhydride 114 on reaction with N-i- r-N-methylhydrazine in acetic acid resulted in the 2,3-benzodiazepinedione derivative 115 in moderate yield. The combination of the less hindered nitrogen (NCH3) and the more reactive carbonyl group in 114 may explain the regioselectivity observed. Functionalisation of C5 by the azido group then led ultimately via the amine 116 and the peptide 117 to the 2,3-benzodiazepine-1,4-diones 118. These final compounds were designed to act as peptidomimetics at the carboxy terminus of hydroxyamides one such compound 118 (R =... 

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