Regioselective N-Acetylation of 4-(2-Hydroxyphenyl)-2-phenyl-2, 3- dihydro-1H-1, 5-benzodiazepine using protection by an intramolecular hydrogen bond

Carlos A. Escobara, Jorge Orellana-Vera, Andrés Vega, Dieter Sicker, Joachim Sieler

Resultado de la investigación: Contribución a una revistaArtículo

5 Citas (Scopus)

Resumen

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.

Idioma originalInglés
Páginas (desde-hasta)969-972
Número de páginas4
PublicaciónZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volumen64
N.º8
EstadoPublicada - 19 ago 2009

Áreas temáticas de ASJC Scopus

  • Química (todo)

Huella Profundice en los temas de investigación de 'Regioselective N-Acetylation of 4-(2-Hydroxyphenyl)-2-phenyl-2, 3- dihydro-1H-1, 5-benzodiazepine using protection by an intramolecular hydrogen bond'. En conjunto forman una huella única.

  • Citar esto