Issue 46, 2018

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

Abstract

Transition metal-free one-pot reaction of quinolines with acylarylacetylenes and water proceeds in the presence of KOH (55–60 °C, MeCN, 48 h) to afford 2-aryl-3-acylquinolines in up to 66% yield. Here, a formal replacement of the acetylene moiety by the aryl and acyl substituents in the quinoline scaffold takes place. In fact, it has been proved experimentally that the reaction involves the ring cleavage, accompanied by the rearrangement and insertion of the electron-deficient acetylene moiety to form a dihydroquinoline intermediate with an aldehyde functional group in position 4. This intermediate gives the corresponding doubly functionalized quinolines.

Graphical abstract: Transition metal-free one-pot double C–H functionalization of quinolines with disubstituted electron-deficient acetylenes

Supplementary files

Article information

Article type
Communication
Submitted
25 Apr 2018
Accepted
10 May 2018
First published
14 May 2018

Chem. Commun., 2018,54, 5863-5866

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

B. A. Trofimov, K. V. Belyaeva, L. P. Nikitina, A. G. Mal'kina, A. V. Afonin, I. A. Ushakov and A. V. Vashchenko, Chem. Commun., 2018, 54, 5863 DOI: 10.1039/C8CC03269F

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