Synthesis 2018; 50(03): 555-564
DOI: 10.1055/s-0036-1591504
paper
© Georg Thieme Verlag Stuttgart · New York

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

Larisa Politanskaya*
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, Ac. Lavrentiev Ave., 9, Novosibirsk 630090, Russian Federation
Novosibirsk State University, Pirogova Street, 2, Novosibirsk 630090, Russian Federation   eMail: plv@nioch.nsc.ru
,
Evgeny Tretyakov
N. N. Vorozhtsov Novosibirsk Institute of Organic Chemistry, Siberian Branch of Russian Academy of Sciences, Ac. Lavrentiev Ave., 9, Novosibirsk 630090, Russian Federation
Novosibirsk State University, Pirogova Street, 2, Novosibirsk 630090, Russian Federation   eMail: plv@nioch.nsc.ru
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Publikationsverlauf

Received: 18. September 2017

Accepted: 02. Oktober 2017

Publikationsdatum:
25. Oktober 2017 (online)


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.

Supporting Information

 
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