Interaction of polyfluorinated 2-chloroquinolines with ammonia

Alexandrina D. Skolyapova, Galina A. Selivanova, Evgeny V. Tretyakov, Tatjana F. Bogdanova, Lyudmila N. Shchegoleva, Irina Yu Bagryanskaya, Larisa Yu Gurskaya, Vitalij D. Shteingarts

Research output: Contribution to journalArticlepeer-review

5 Citations (Scopus)

Abstract

We have studied the interaction of polyfluorinated (in the benzene moiety) 2-chloroquinolines with liquid and aqueous ammonia as an approach to the synthesis of halogen-containing aminoquinolines. 5,7-Difluoro-, 5,6,8-trifluoro-, and 5,7,8-trifluoro-2-chloroquinolines mostly form products of substitution of the Cl atom, whereas 5,7-difluoro-2,6-dichloroquinoline, 5,6,7,8-tetrafluoro-, and 6,7-difluoro-2-chloroquinolines yield products of substitution of an F atom at various positions. The replacement of liquid ammonia with aqueous causes an increase in the proportion of the products of aminodechlorination relative to the products of aminodefluorination. For 2-chloro-6,8-difluoroquinoline this replacement leads to 2-amino-6,8-difluoroquinoline as the main product instead of the 8-amino-derivative. Activation energy values estimated by DFT calculations for the reactions in question agree with the reaction regioselectivity observed experimentally.

Original languageEnglish
Pages (from-to)1219-1229
Number of pages11
JournalTetrahedron
Volume73
Issue number9
DOIs
Publication statusPublished - 2 Mar 2017

Keywords

  • Ammonia
  • DFT calculations
  • Nucleophilic substitution
  • Polyfluorinated 2-chloroquinolines
  • Polyfluorinated aminoquinolines
  • BENZENE-RING
  • KINASE INHIBITORS
  • REGIOSELECTIVITY
  • IDENTIFICATION
  • LIQUID-AMMONIA
  • NUCLEOPHILIC AROMATIC-SUBSTITUTION
  • BIOLOGICAL EVALUATION
  • FLUORINE
  • ANTAGONISTS
  • DERIVATIVES

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