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

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-benz...

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Published in:Chemistry of heterocyclic compounds (New York, N.Y. 1965) N.Y. 1965), 2009-11, Vol.45 (11), p.1379-1387
Main Authors: Pavlovsky, V. I., Semenishina, E. A., Andronati, S. A., Filippova, I. G., Simonov, Yu. A., Gdaniec, M., Lipkowski, J.
Format: Article
Language:English
Subjects:
Chemistry
Chemistry and Materials Science
Organic Chemistry
Pharmacy
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Summary: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.
ISSN:0009-3122
1573-8353
DOI:10.1007/s10593-010-0436-y