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: Article

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

Huella dactilar

Acetylation
Hydrogen bonds
Nucleophiles
Benzodiazepines
Hydroxyl Radical
Crystal structure
Temperature
4-(2-hydroxyphenyl)-2-phenyl-2,3-dihydro-1H-1,5-benzodiazepine
acetic anhydride

ASJC Scopus subject areas

  • Chemistry(all)

Citar esto

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title = "Regioselective N-Acetylation of 4-(2-Hydroxyphenyl)-2-phenyl-2, 3- dihydro-1H-1, 5-benzodiazepine using protection by an intramolecular hydrogen bond",
abstract = "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.",
keywords = "1, 5-Benzodiazepine, Intramolecular Hydrogen Bond, N-Acetylation, Protecting Group Effect, Regioselectivity",
author = "Escobara, {Carlos A.} and Jorge Orellana-Vera and Andr{\'e}s Vega and Dieter Sicker and Joachim Sieler",
year = "2009",
month = "8",
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language = "English",
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journal = "Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences",
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TY - JOUR

T1 - Regioselective N-Acetylation of 4-(2-Hydroxyphenyl)-2-phenyl-2, 3- dihydro-1H-1, 5-benzodiazepine using protection by an intramolecular hydrogen bond

AU - Escobara, Carlos A.

AU - Orellana-Vera, Jorge

AU - Vega, Andrés

AU - Sicker, Dieter

AU - Sieler, Joachim

PY - 2009/8/19

Y1 - 2009/8/19

N2 - 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.

AB - 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.

KW - 1, 5-Benzodiazepine

KW - Intramolecular Hydrogen Bond

KW - N-Acetylation

KW - Protecting Group Effect

KW - Regioselectivity

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M3 - Article

AN - SCOPUS:68649096201

VL - 64

SP - 969

EP - 972

JO - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

JF - Zeitschrift fur Naturforschung - Section B Journal of Chemical Sciences

SN - 0932-0776

IS - 8

ER -