SPECIAL FEATURES OF THE ALKYLATION OF 7-BROMO-5-(2-CHLOROPHENYL)-3-HYDROXY-1,2-DIHYDRO-3H-1,4-BENZODIAZEPIN-2-ONE WITH ALKYL TOSYLATES

Authors

  • В. И. Павловский A.V. Bogatsky of Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa 65080
  • Е. А. Семенишина A.V. Bogatsky of Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa 65080
  • С. А. Андронати A.V. Bogatsky of Physico-Chemical Institute, National Academy of Sciences of Ukraine, Odessa 65080
  • И. Г. Филиппова Institute of Applied Physics, Academy of Sciences of Moldova, Kishinev MD-2028
  • Ю. А. Симонов Institute of Applied Physics, Academy of Sciences of Moldova, Kishinev MD-2028
  • М. Гданец Department of Chemistry, A. Mickiewicz University, 60-780 Poznan
  • Я. Липковский Institute of Physical Chemistry, Polish Academy of Sciences, Warsaw 01-224

DOI:

https://doi.org/10.1007/6452

Keywords:

1, 4-benzodiazepine, molecular and crystal structure, prototropic migration, synthesis

Abstract

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.

How to Cite
Pavlovsky, V. I.; Semenishina, E. A.; Andronati, S. A.; Filippova, I. G.;
Simonov, Yu. A.; Gdaniec, M.; Lipkowski, J. Chem. Heterocycl. Compd. 2009, 45, 1379. [Khim. Geterotsikl. Soedin. 2009, 1714.]

For this article in the English edition see DOI 10.1007/s10593-010-0436-y

 

 

 

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Published

2021-10-07

Issue

No. 11 (2009)

Section

Original Papers