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Reaction of quinolines fluorinated at the benzene ring with nitrogen-centered nucleophiles Научная публикация

Журнал Russian Chemical Bulletin
ISSN: 1066-5285 , E-ISSN: 1573-9171
Вых. Данные Год: 2009, Том: 58, Номер: 5, Страницы: 1049-1061 Страниц : DOI: 10.1007/s11172-009-0134-z
Ключевые слова fluorinated quinolines; ammonia; piperidine; hydrazine hydrate; aromatic nucleophilic substitution; fluorinated aminoquinolines
Авторы Safina L. Yu. 1 , Selivanova G. A. 1 , Bagryanskaya I. Yu. 1 , Shteingarts V. D. 1,2
Организации
1 (Данные Web of science) Russian Acad Sci, NN Vorozhtsov Inst Organ Chem, Siberian Branch, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, Novosibirsk 630090, Russia

Реферат: A primary functionalization of quinolines polyfluorinated at the benzene ring (5,7-difluoro-, 5,7,8-trifluoro-, 5,6,8-trifluoro-, 8-chloro-5,7-difluoro-, 5,6,7,8-tetrafluoro-, and 5,7,8-trifluoro-6-(trifluoromethyl)quinolines) by the reaction with nitrogen-centered nucleophiles (aqueous and liquid ammonia, hydrazine hydrate, piperidine) has been studied. If the molecule of fluorinated quinoline contains three or four halogen atoms, their combined orientation effect outweighs the influence of the heterocycle N atom. It was found that the orientation of substitution in the reactions of 5,6,8-trifluoro- and 5,7,8-trifluoro-6-(trifluoromethyl)quinolines with piperidine depends on temperature, because the enthalpy control of the ratio of the rates of competing reactions changes to the entropy control. Nineteen new quinoline derivatives containing F atoms and amino or modified amino groups in the benzene ring have been obtained.
Библиографическая ссылка: Safina L.Y. , Selivanova G.A. , Bagryanskaya I.Y. , Shteingarts V.D.
Reaction of quinolines fluorinated at the benzene ring with nitrogen-centered nucleophiles
Russian Chemical Bulletin. 2009. V.58. N5. P.1049-1061. DOI: 10.1007/s11172-009-0134-z WOS Scopus РИНЦ OpenAlex
Даты:
Опубликована в печати: 1 мая 2009 г.
Опубликована online: 17 апр. 2010 г.
Идентификаторы БД:
Web of science: WOS:000276772100025
Scopus: 2-s2.0-77955729938
РИНЦ: 15312996
OpenAlex: W2062280255
Цитирование в БД:
БД Цитирований
Web of science 6
Scopus 8
РИНЦ 8
OpenAlex 8
Альметрики: