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

Lamiaa Ouchakour, Melinda Nonn, Matthias D'hooghe, Loránd Kiss

Research output: Contribution to journalArticle

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.

Original languageEnglish
Article number109466
JournalJournal of Fluorine Chemistry
Volume232
DOIs
Publication statusPublished - Apr 2020

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Keywords

  • Azaheterocycle
  • Benzazepine
  • Fluorine
  • Reductive amination
  • Ring closing
  • Ring expansion

ASJC Scopus subject areas

  • Biochemistry
  • Environmental Chemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry
  • Inorganic Chemistry

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