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p-Toluenesulfonic Acid Induced Conversion of Fluorinated Trimethylsilylethynylanilines into Aminoacetophenones: Versatile Precursors for the Synthesis of Benzoazaheterocycles Научная публикация

Журнал Synthesis
ISSN: 0039-7881
Вых. Данные Год: 2018, Том: 50, Номер: 3, Страницы: 555-564 Страниц : 10 DOI: 10.1055/s-0036-1591504
Ключевые слова alkynes; hydration; polyfluoroarenes; aryl methyl ketones; polyfluorinated azaheterocycles
Авторы Politanskaya Larisa 1,2 , Tretyakov Evgeny 1,2
Организации
1 N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch, Russian Academy of Sciences, Ac. Lavrentiev Ave., 9, Novosibirsk, 630090, Russian Federation
2 Novosibirsk State University, Pirogova Street, 2, Novosibirsk, 630090, Russian Federation

Реферат: A simple and efficient approach to the synthesis of fluorinated amino-substituted acetophenones in good to excellent yields is reported. The heart of the proposed method consists of conversion of a Me3Si-C=C-moiety into a MeC(=O)-group in the presence of p-toluenesulfonic acid (p-TSA) passing a stage of ethynylaniline formation. The reaction is metal-free, proceeds under mild conditions, and uses readily available starting compounds (trimethylsilylarylacetylene derivatives). The reaction provides access to amino-substituted acetophenones, which may serve as precursors for the synthesis of polyfluorinated azaheterocycles, having potential anticarcinogenic activity.
Библиографическая ссылка: Politanskaya L. , Tretyakov E.
p-Toluenesulfonic Acid Induced Conversion of Fluorinated Trimethylsilylethynylanilines into Aminoacetophenones: Versatile Precursors for the Synthesis of Benzoazaheterocycles
Synthesis. 2018. V.50. N3. P.555-564. DOI: 10.1055/s-0036-1591504 WOS Scopus РИНЦ OpenAlex
Даты:
Опубликована online: 25 окт. 2017 г.
Опубликована в печати: 1 февр. 2018 г.
Идентификаторы БД:
Web of science: WOS:000422936300011
Scopus: 2-s2.0-85032378694
РИНЦ: 35505201
OpenAlex: W2765740623
Цитирование в БД:
БД Цитирований
Web of science 15
Scopus 16
РИНЦ 17
OpenAlex 18
Альметрики: