Interaction of polyfluorinated 2-chloroquinolines with ammonia | Sciact

Interaction of polyfluorinated 2-chloroquinolines with ammonia Научная публикация

Журнал

Tetrahedron
ISSN: 0040-4020

Вых. Данные

Год: 2017, Том: 73, Номер: 9, Страницы: 1219-1229 Страниц : 11 DOI: 10.1016/j.tet.2017.01.026

Ключевые слова

Polyfluorinated 2-chloroquinolines; Nucleophilic substitution; Ammonia; Polyfluorinated aminoquinolines; DFT calculations

Авторы

Skolyapova Alexandrina D. ¹ , Selivanova Galina A. ¹ , Tretyakov Evgeny V. ¹ , Bogdanova Tatjana F. ¹ , Shchegoleva Lyudmila N. ¹ , Bagryanskaya Irina Yu. ^1,2 , Gurskaya Larisa Yu. ¹ , Shteingarts Vitalij D. ¹

Организации

1	(Данные Web of science) N N Vorozhtsov Novosibirsk Inst Organ Chem, 9 Ac Lavrentiev Ave, Novosibirsk 630090, Russia
2	(Данные Web of science) Novosibirsk State Univ, 2 Pirogova Str, Novosibirsk 630090, Russia

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.

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 OpenAlex

Опубликована в печати:

1 мар. 2017 г.

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

БД	Цитирований
Web of science	8
Scopus	9
РИНЦ	10
OpenAlex	9