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Transition metal-free one-pot double C-H-functionalization of quinolines by disubstituted electron-deficient acetylenes

Abstract

Transition metal-free one-pot reaction of quinolines with acylarylacetylenes and water in the presence of KOH (55-60 oC, MeCN, 48 h) affords 2-aryl-3-acylquinolines in up to 66% yield. Here, a formal replacement of acetylene moiety by that with aryl and acyl substituents in the quinoline scaffold takes place. In fact as it is experimentally proved the reaction involves the ring cleavage, accompanied by the rearrangement and insertion of the electron-deficient acetylene moiety to form the dihydroquinoline intermediate with aldehyde function in the position 4. The latter eliminates an aldehyde to give the corresponding doubly functionalized quinolines.

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Publication details

The article was received on 25 Apr 2018, accepted on 10 May 2018 and first published on 14 May 2018


Article type: Communication
DOI: 10.1039/C8CC03269F
Citation: Chem. Commun., 2018, Accepted Manuscript
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    Transition metal-free one-pot double C-H-functionalization of quinolines by disubstituted electron-deficient acetylenes

    B. Trofimov, K. Belyaeva, L. Nikitina, A. Mal’kina, A. Afonin, I. Ushakov and A. V. Vashchenko, Chem. Commun., 2018, Accepted Manuscript , DOI: 10.1039/C8CC03269F

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