Since the amino and the hydroxyl groups of 4-(2-hydroxyphenyl)-2-phenyl-2, 3-dihydro-1H-1, 5- benzodiazepine can both act as nucleophiles, the introduction of both an N-acetyl and an O-acetyl group is expected when the compound is allowed to react with an excess of an electrophile such as acetic anhydride. An intramolecular hydrogen bond between OH and N-5 of the benzodiazepine has been used to obtain differentiation between the two possible sites of acetylation. Thus, this feature offers a preparatively utilizable protecting effect for the OH group and allows for a regioselective N-acetylation at ambient temperature. Both mono- and diacetylated compounds were prepared and characterized by crystal structure analysis.
|Number of pages||4|
|Journal||Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences|
|Publication status||Published - 2009|
- 1, 5-Benzodiazepine
- Intramolecular Hydrogen Bond
- Protecting Group Effect
ASJC Scopus subject areas