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Synthesis and properties of 2,2,4-trisubstituted 2,3-dihydro-1H-1,5-benzodiazepines

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Chemistry of Heterocyclic Compounds Aims and scope

Abstract

General conditions for the condensation of acetylarenes with o-phenylenediamine hydrochloride, leading to the formation of 2,4-diaryl-2-methyl-2,3-dihydro-1H-1,5-benzodiazepines, have been worked out. It has been shown that this reaction is an equilibrium one, that the equilibrium is extremely sensitive to the amount of water in the reaction medium, and that the process takes place with the formation of bisazomethines as intermediates. The UV, IR, and PMR spectra and the dipole moments of the heterocyclic compounds obtained are discussed.

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Literature cited

  1. J. Exeley and P. Wells, Chem. Ber., 38, 2259 (1905).

    Google Scholar 

  2. Q. Q. Dang, R. Gaujolle, and T. B. Dang, C. R. Acad. Sci. Paris, 272, 1518 (1971).

    Google Scholar 

  3. P. S. Reddi, C. V. Patham, and S. N. V. Rao, Indian J. Chem., 10, 982 (1972).

    Google Scholar 

  4. J. Herbert and H. J. Suschiky, J. Chem. Soc. Perkin Trans. I, 2657 (1974).

    Google Scholar 

  5. V. D. Orlov, N. N. Kolos, F. G. Yaremenko, and V. F. Lavrushin, Khim. Geterotsikl. Soedin., No. 5, 697 (1980).

    Google Scholar 

  6. F. G. Yaremenko, V. D. Orlov, N. N. Kolos, and V. F. Lavrushin, Izv. Vyssh. Uchebn. Zaved., Khim. Khim. Tekhnol., 23, 831 (1980).

    Google Scholar 

  7. V. D. Orlov, N. N. Kolos, and B. M. Zolotarev, Khim. Geterotsikl. Soedin., No. 3, 390 (1983).

    Google Scholar 

  8. O. A. Osipov, V. I. Minkin, and A. D. Garnovskii, Handbook of Dipole Moments [in Russian], Vysshaya Shkola, Moscow (1971), pp. 183, 291.

    Google Scholar 

  9. V. D. Orlov, N. N. Kolos, S. M. Desenko, and V. F. Lavrushin, Khim. Geterotsikl. Soedin., No. 6, 830 (1982).

    Google Scholar 

  10. D. D. Perrin, Dissociation Constants of Organic Bases in Aqueous Solution, Butterworth, London (1965), p. 473.

    Google Scholar 

  11. S. V. Tsukerman, V. D. Orlov, Yu. N. Surov, and V. F. Lavrushin, Zh. Strukt. Khim., 9 67 (1968).

    Google Scholar 

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Authors and Affiliations

  1. A. M. Gor'kii Khar'kov State University, USSR

    V. D. Orlov, S. M. Desenko & N. N. Kolos

Authors
  1. V. D. Orlov
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  2. S. M. Desenko
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  3. N. N. Kolos
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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 1, pp. 126–131, January, 1984.

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Orlov, V.D., Desenko, S.M. & Kolos, N.N. Synthesis and properties of 2,2,4-trisubstituted 2,3-dihydro-1H-1,5-benzodiazepines. Chem Heterocycl Compd 20, 106–111 (1984). https://doi.org/10.1007/BF00505862

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  • DOI: https://doi.org/10.1007/BF00505862

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