Standard

Interaction of polyfluorinated 2-chloroquinolines with ammonia. / Skolyapova, Alexandrina D.; Selivanova, Galina A.; Tretyakov, Evgeny V. et al.

In: Tetrahedron, Vol. 73, No. 9, 02.03.2017, p. 1219-1229.

Research output: Contribution to journal › Article › peer-review

Harvard

Skolyapova, AD, Selivanova, GA, Tretyakov, EV, Bogdanova, TF, Shchegoleva, LN, Bagryanskaya, IY, Gurskaya, LY & Shteingarts, VD 2017, 'Interaction of polyfluorinated 2-chloroquinolines with ammonia', Tetrahedron, vol. 73, no. 9, pp. 1219-1229. https://doi.org/10.1016/j.tet.2017.01.026

APA

Skolyapova, A. D., Selivanova, G. A., Tretyakov, E. V., Bogdanova, T. F., Shchegoleva, L. N., Bagryanskaya, I. Y., Gurskaya, L. Y., & Shteingarts, V. D. (2017). Interaction of polyfluorinated 2-chloroquinolines with ammonia. Tetrahedron, 73(9), 1219-1229. https://doi.org/10.1016/j.tet.2017.01.026

Vancouver

Skolyapova AD, Selivanova GA, Tretyakov EV, Bogdanova TF, Shchegoleva LN, Bagryanskaya IY et al. Interaction of polyfluorinated 2-chloroquinolines with ammonia. Tetrahedron. 2017 Mar 2;73(9):1219-1229. doi: 10.1016/j.tet.2017.01.026

Author

Skolyapova, Alexandrina D. ; Selivanova, Galina A. ; Tretyakov, Evgeny V. et al. / Interaction of polyfluorinated 2-chloroquinolines with ammonia. In: Tetrahedron. 2017 ; Vol. 73, No. 9. pp. 1219-1229.

BibTeX

@article{35d558b7c0854a50aa3e1c090aae1b42,
title = "Interaction of polyfluorinated 2-chloroquinolines with ammonia",
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.",
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",
author = "Skolyapova, {Alexandrina D.} and Selivanova, {Galina A.} and Tretyakov, {Evgeny V.} and Bogdanova, {Tatjana F.} and Shchegoleva, {Lyudmila N.} and Bagryanskaya, {Irina Yu} and Gurskaya, {Larisa Yu} and Shteingarts, {Vitalij D.}",
year = "2017",
month = mar,
day = "2",
doi = "10.1016/j.tet.2017.01.026",
language = "English",
volume = "73",
pages = "1219--1229",
journal = "Tetrahedron",
issn = "0040-4020",
publisher = "Elsevier",
number = "9",

}

RIS

TY - JOUR

T1 - Interaction of polyfluorinated 2-chloroquinolines with ammonia

AU - Skolyapova, Alexandrina D.

AU - Selivanova, Galina A.

AU - Tretyakov, Evgeny V.

AU - Bogdanova, Tatjana F.

AU - Shchegoleva, Lyudmila N.

AU - Bagryanskaya, Irina Yu

AU - Gurskaya, Larisa Yu

AU - Shteingarts, Vitalij D.

PY - 2017/3/2

Y1 - 2017/3/2

N2 - 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.

AB - 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.

KW - Ammonia

KW - DFT calculations

KW - Nucleophilic substitution

KW - Polyfluorinated 2-chloroquinolines

KW - Polyfluorinated aminoquinolines

KW - BENZENE-RING

KW - KINASE INHIBITORS

KW - REGIOSELECTIVITY

KW - IDENTIFICATION

KW - LIQUID-AMMONIA

KW - NUCLEOPHILIC AROMATIC-SUBSTITUTION

KW - BIOLOGICAL EVALUATION

KW - FLUORINE

KW - ANTAGONISTS

KW - DERIVATIVES

UR - http://www.scopus.com/inward/record.url?scp=85010408109&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2017.01.026

DO - 10.1016/j.tet.2017.01.026

M3 - Article

AN - SCOPUS:85010408109

VL - 73

SP - 1219

EP - 1229

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 9

ER -

ID: 10314903