p-Toluenesulfonic Acid Induced Conversion of Fluorinated Trimethylsilylethynylanilines into Aminoacetophenones: Versatile Precursors for the Synthesis of Benzoazaheterocycles Full article
| Journal |
Synthesis
ISSN: 0039-7881 |
||||
|---|---|---|---|---|---|
| Output data | Year: 2018, Volume: 50, Number: 3, Pages: 555-564 Pages count : 10 DOI: 10.1055/s-0036-1591504 | ||||
| Tags | alkynes; hydration; polyfluoroarenes; aryl methyl ketones; polyfluorinated azaheterocycles | ||||
| Authors |
|
||||
| Affiliations |
|
Abstract:
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.
Cite:
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
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
Dates:
| Published online: | Oct 25, 2017 |
| Published print: | Feb 1, 2018 |
Identifiers:
| Web of science | WOS:000422936300011 |
| Scopus | 2-s2.0-85032378694 |
| Elibrary | 35505201 |
| OpenAlex | W2765740623 |