Synthesis of polyfluorinated aminoquinolines via nitroquinolines

Alexandrina D. Skolyapova, Galina A. Selivanova, Evgeny V. Tretyakov, Irina Yu Bagryanskaya, Vitalij D. Shteingarts

Research output: Contribution to journalArticlepeer-review

1 Citation (Scopus)

Abstract

Transformation of 14 quinolines polyfluorinated in the benzene moiety was investigated in nitration systems: a mixture of HNO3 and H2SO4, NaNO3 in H2SO4, NO2BF3OH in sulfolane, or NaNO3 in oleum. 5-Nitro- and/or 8-nitro derivatives formed if positions 5 or 8 were unoccupied in the starting compounds. Otherwise, nitro products were not detectable, and the initial compounds were oxidized. In some cases, F atoms at the ortho position relative to the nitro group were substituted thus affording hydroxynitroquinolines. Polyfluorinated 2-chloroquinolines were nitrated more easily than were quinolines not containing a substituent at position 2. Thus, a method is proposed for reduction of nitroquinolines to aminoquinolines that are not available via other approaches.

Original languageEnglish
Pages (from-to)14-23
Number of pages10
JournalJournal of Fluorine Chemistry
Volume211
DOIs
Publication statusPublished - 1 Jul 2018

Keywords

  • Nitration
  • Polyfluorinated aminoquinolines
  • Polyfluorinated quinolines
  • Reduction of nitroquinolines

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