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Special features of the alkylation of 7-bromo-5-(2-chlorophenyl)- 3-hydroxy-1,2-dihydro-3h-1,4-benzo- diazepin-2-one with alkyl tosylates

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Chemistry of Heterocyclic Compounds Aims and scope

On interacting 7-bromo-5-(2-chlorophenyl)-3-hydroxy-1,2-dihydro-3H-1,4-benzodiazepin-2-one with methyl, hexyl, dodecyl, and cetyl tosylates, 1-alkyl-7-bromo-5-(2-chlorophenyl)-1,2,4,5-tetrahydro-3H-1,4-benzodiazepin-2,3-diones, and 1-alkyl-7-bromo-5-(2-chlorophenyl)-3-hydroxy-1,2-dihydro-3H-1,4-benzodiazepin- 2-ones were obtained. Only the dione was formed in the case of hexyl tosylate. On alkylating with methyl tosylate only the 3-hydroxy derivative was formed. It was shown that at pH 14 the 1-cetyl and 1-dodecyl-3-hydroxy derivatives were completely converted into the corresponding diones. The molecular and crystal structures of the compounds were established by X-ray structural analysis.

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Authors and Affiliations

  1. A.V. Bogatsky of Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa, 65080, Ukraine

    V. I. Pavlovsky, E. A. Semenishina & S. A. Andronati

  2. Institute of Applied Physics, Academy of Sciences of Moldova, Kishinev, MD-2028, Republic of Moldova

    I. G. Filippova & Yu. A. Simonov

  3. Department of Chemistry, A. Mickiewicz University, 60-780, Poznan, Poland

    M. Gdaniec

  4. Institute of Physical Chemistry, Polish Academy of Sciences, Warsaw, 01-224, Poland

    J. Lipkowski

Authors
  1. V. I. Pavlovsky
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  2. E. A. Semenishina
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  3. S. A. Andronati
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  4. I. G. Filippova
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  5. Yu. A. Simonov
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  6. M. Gdaniec
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  7. J. Lipkowski
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Correspondence to V. I. Pavlovsky.

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Translated from Khimiya Geterotsiklicheskikh Soedinenii, No. 11, pp. 1714–1724, November, 2009.

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Pavlovsky, V.I., Semenishina, E.A., Andronati, S.A. et al. Special features of the alkylation of 7-bromo-5-(2-chlorophenyl)- 3-hydroxy-1,2-dihydro-3h-1,4-benzo- diazepin-2-one with alkyl tosylates. Chem Heterocycl Comp 45, 1379–1387 (2009). https://doi.org/10.1007/s10593-010-0436-y

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  • DOI: https://doi.org/10.1007/s10593-010-0436-y

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