Synthesis of Aromatic Derivatives of 1,5-Benzodiazepine in the Reaction of 4-Nitro-o-phenylenediamine with Chalcone Dibromides

Article abstract of DOI:10.1007/BF01170744

The reaction of 4-nitro-o-phenylenediamine with 4-nitro-4'-R-chalcone dibromides affords the corresponding β-(2-amino-4-nitroanilino)chalcones; x-ray diffraction data indicate that these are the Z-isomers.Experiments have been performed to determine the conditions required for cyclization of these compounds into 2,4-diaryl-7(8)-nitro-1,5-benzodiazepines.In the solid phase or in ethanol solutions, these compounds exist primarily in the 3H tautomeric form; but in DMSO solutions, the 1H form predominates.