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

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

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.

Original languageEnglish
Pages (from-to)969-972
Number of pages4
JournalZeitschrift fur Naturforschung - Section B Journal of Chemical Sciences
Volume64
Issue number8
DOIs
Publication statusPublished - 2009

Keywords

  • 1, 5-Benzodiazepine
  • Intramolecular Hydrogen Bond
  • N-Acetylation
  • Protecting Group Effect
  • Regioselectivity

ASJC Scopus subject areas

  • Chemistry(all)

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