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The p-Toluenesulfonic Acid-Catalyzed Transformation of Polyfluorinated 2-Alkynylanilines to 2-Aminoarylketones and Indoles Full article

Journal Tetrahedron Letters
ISSN: 0040-4039
Output data Year: 2015, Volume: 56, Number: 39, Pages: 5328-5332 Pages count : 5 DOI: 10.1016/j.tetlet.2015.07.078
Tags p-TSA-catalyzed hydration, Polyfluorinated 2-alkynylanilines, Polyfluorinated 2-aminoarylketones, Polyfluorinated indoles
Authors Politanskaya Larisa 1 , Shteingarts Vitalij 1 , Tretyakov Evgeny 1,3 , Potapov Alexander 2,3
Affiliations
1 N.N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, Ak. Lavrentiev Avenue 9, 630090 Novosibirsk, Russian Federation
2 Boreskov Institute of Catalysis, Siberian Branch of Russian Academy of Sciences, Ak. Lavrentiev Avenue 5, 630090 Novosibirsk, Russian Federation
3 Novosibirsk State University, Pirogova Street, 2, 630090 Novosibirsk, Russian Federation

Funding (1)

1 Russian Foundation for Basic Research 14-03-00108

Abstract: The reactivity of a series of polyfluorinated 2-alkynylanilines with various alcohols using p-TSA has been studied. It was found that hydration of the triple bond gave rise to polyfluorinated 2-aminoarylketones and competed with an electrophilic heterocyclization reaction leading to polyfluorinated indoles. The dependence of the reaction pathways on the nature of the alkynylaniline substituents has been examined.
Cite: Politanskaya L. , Shteingarts V. , Tretyakov E. , Potapov A.
The p-Toluenesulfonic Acid-Catalyzed Transformation of Polyfluorinated 2-Alkynylanilines to 2-Aminoarylketones and Indoles
Tetrahedron Letters. 2015. V.56. N39. P.5328-5332. DOI: 10.1016/j.tetlet.2015.07.078 WOS Scopus РИНЦ ANCAN OpenAlex
Dates:
Submitted: Jun 9, 2015
Accepted: Jul 29, 2015
Published online: Aug 3, 2015
Published print: Sep 1, 2015
Identifiers:
Web of science: WOS:000361252200004
Scopus: 2-s2.0-84939653656
Elibrary: 24469299
Chemical Abstracts: 2015:1273247
Chemical Abstracts (print): 163:473848
OpenAlex: W1070156391
Citing:
DB Citing
Web of science 11
Scopus 11
Elibrary 12
OpenAlex 12
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