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

Authors

  • H. H. Колос Kharkov State University, Kharkov 310077
  • B. Д. Орлов Kharkov State University, Kharkov 310077
  • E. Я. Юзефовская Kharkov State University, Kharkov 310077
  • Ф. Г. Яременко Kharkov State University, Kharkov 310077
  • H. П. Воробьева Kharkov State University, Kharkov 310077
  • O. B. Шишкин Kharkov State University, Kharkov 310077
  • Ю. T. Стручков A. N. Nesmeyanov Institute of Organoelement Compounds, Russian Academy of Sciences, Moscow 117813
  • С. M. Ивков Kharkov State University, Kharkov 310077

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 performed 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.

How to Cite
Kolos, N. N.; Orlov, V. D.; Yuzefovskaya, E. Y.; Yaremenko, F. G.; Vorob'eva, N. P.; Shishkin, O. V.; Struchkov, Yu. T.; Ivkov, S. M. Chem. Heterocycl. Compd. 1995, 31, 827. [Khim. Geterotsikl. Soedin. 1995, 950.]

For this article in the English edition, see DOI https://doi.org/10.1007/BF01170744

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Published

1995-07-25

Issue

No. 7 (1995)

Section

Original Papers