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. (C) 2017 Elsevier Ltd. All rights reserved.

Cite: Skolyapova A.D. , Selivanova G.A. , Tretyakov E.V. , Bogdanova T.F. , Shchegoleva L.N. , Bagryanskaya I.Y. , Gurskaya L.Y. , Shteingarts V.D.
Interaction of polyfluorinated 2-chloroquinolines with ammonia
Tetrahedron. 2017. V.73. N9. P.1219-1229. DOI: 10.1016/j.tet.2017.01.026 WOS Scopus РИНЦ

Dates:

Published print:

Mar 1, 2017

Identifiers:

Web of science	WOS:000394193900002
Scopus	2-s2.0-85010408109
Elibrary	29477301
OpenAlex	W2574290945

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