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Synthesis of polyfluorinated 4-hydroxyquinolin-2(1H)-ones based on the cyclization of 2-alkynylanilines with carbon dioxide Full article

Journal Journal of Fluorine Chemistry
ISSN: 0022-1139
Output data Year: 2021, Volume: 242, Article number : 109720, Pages count : DOI: 10.1016/j.jfluchem.2020.109720
Tags Polyfluorinated alkynylanilines; Polyfluorinated heterocycles; Carbon dioxide incorporation; Intermolecular heterocyclization reaction
Authors Politanskaya Larisa 1 , Tretyakov Evgeny 1,2 , Xi Chanjuan 3
Affiliations
1 (Данные Web of science) Russian Acad Sci, NN Vorozhtsov Novosibirsk Inst Organ Chem, Siberian Branch, Ac Lavrentiev Ave 9, Novosibirsk 630090, Russia
2 (Данные Web of science) Novosibirsk State Univ, Pirogova St 2, Novosibirsk 630090, Russia
3 (Данные Web of science) Tsinghua Univ, Dept Chem, MOE Key Lab Bioorgan Phosphorus Chem & Chem Biol, Beijing 100084, Peoples R China

Abstract: Convenient and efficient synthesis of polyfluorinated 4-hydroxyquinolin-2(1H)-ones from the corresponding oalkynylaniline derivatives and CO2 (1 atm), mediated by 1,8-diazabicyclo[5.4.0]undec-7-ene (DBU) and AgNO3 in acetonitrile was performed. This synthetic methodology may be used to prepare fluorinated heterocycles containing peripheral alkynyl and amino groups but is not suitable for silylethynyl derivatives that give indoles as the main products. The reaction takes place under mild conditions (60 degrees C) and involves readily available starting materials that include cheap and renewable carbon dioxide.
Cite: Politanskaya L. , Tretyakov E. , Xi C.
Synthesis of polyfluorinated 4-hydroxyquinolin-2(1H)-ones based on the cyclization of 2-alkynylanilines with carbon dioxide
Journal of Fluorine Chemistry. 2021. V.242. 109720 . DOI: 10.1016/j.jfluchem.2020.109720 WOS Scopus РИНЦ
Dates:
Published print: Feb 1, 2021
Identifiers:
Web of science WOS:000609574500015
Scopus 2-s2.0-85099185842
Elibrary 45016410
OpenAlex W3115013338
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