Interaction of polyfluorinated 2-chloroquinolines with ammonia

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 substit...

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Bibliographic Details
Published in:Tetrahedron 2017-03, Vol.73 (9), p.1219-1229
Main Authors: Skolyapova, Alexandrina D., Selivanova, Galina A., Tretyakov, Evgeny V., Bogdanova, Tatjana F., Shchegoleva, Lyudmila N., Bagryanskaya, Irina Yu, Gurskaya, Larisa Yu, Shteingarts, Vitalij D.
Format: Article
Language:English
Subjects:
Ammonia
DFT calculations
Nucleophilic substitution
Polyfluorinated 2-chloroquinolines
Polyfluorinated aminoquinolines
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Summary: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. [Display omitted]
ISSN:0040-4020
1464-5416
DOI:10.1016/j.tet.2017.01.026