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Synthesis of aromatic derivatives of 1,5-benzodiazepine in the reaction of 4-nitro-o-phenylenediamine with chalcone dibromides

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

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 perfortned to determine the conditions required for cyclization of these compounds into 2, 4-diaryl7(8)-nitro-1, 5-benzodiazepines. In the solid phase or in ethanol solutions, these latter compounds exist primarily in the 3H tautomeric form; but in DMSO solutions, the 1H form predominates.

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Authors
  1. N. N. Kolos
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  2. V. D. Orlov
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  3. E. Ya. Yuzefovskaya
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  4. F. G. Yaremenko
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  5. N. P. Vorob'eva
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  6. O. V. Shishkin
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  7. Yu. T. Struchkov
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  8. S. M. Ivkov
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Additional information

Khar'kov State University, Khar'kov 310077. Institute of Heteroorganic Chemistry, Russian Academy of Sciences, Moscow 117813. Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 7, pp. 950–958, July, 1995. Original article submitted June 30, 1994; revision submitted April 3, 1995.

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Kolos, N.N., Orlov, V.D., Yuzefovskaya, E.Y. et al. Synthesis of aromatic derivatives of 1,5-benzodiazepine in the reaction of 4-nitro-o-phenylenediamine with chalcone dibromides. Chem Heterocycl Compd 31, 827–834 (1995). https://doi.org/10.1007/BF01170744

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  • DOI: https://doi.org/10.1007/BF01170744

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