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A de novo synthetic method to the access of N-substituted benzazepines

Authors
  • Ouchakour, Lamiaa
  • Nonn, Melinda
  • D'hooghe, Matthias
  • Kiss, Lorand
Publication Date
Jan 01, 2020
Identifiers
DOI: 10.1016/j.jfluchem.2020.109466
OAI: oai:archive.ugent.be:8691845
Source
Ghent University Institutional Archive
Keywords
Language
English
License
White
External links

Abstract

A novel, convenient procedure has been described for the construction of fluorine-containing benzazepines. The synthetic protocol starting from readily available dihydronaphthalene regioisomers is based on oxidative ring olefin bond cleavage followed by ring closure of the diformyl intermediates in the presence of some fluorine-containing primary amines across double reductive amination. The applicability of the developed synthetic method was demonstrated by the synthesis of 13 benzazepine compounds isolated in 22-35 % overall yields.

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