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Issue 43, 2018
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Catalyst-free 1 : 2 annulation of quinolines with trifluoroacetylacetylenes: an access to functionalized oxazinoquinolines

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Abstract

Metal- and solvent-free reaction of quinolines with two molecules of aryltrifluoroacetylacetylenes afforded 3-arylethynyl-3-trifluoromethyl-1,3-oxazinoquinolines in up to 92% yields. The formation of a zwitterionic intermediate in the first step triggered a multistep domino reaction. This one-pot synthesis opens an easy access to novel quinoline derivatives bearing trifluoromethyl, acetylene and ketone functions, thus providing a powerful tool for drug design.

Graphical abstract: Catalyst-free 1 : 2 annulation of quinolines with trifluoroacetylacetylenes: an access to functionalized oxazinoquinolines

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Publication details

The article was received on 25 Sep 2018, accepted on 11 Oct 2018 and first published on 12 Oct 2018


Article type: Communication
DOI: 10.1039/C8OB02379D
Citation: Org. Biomol. Chem., 2018,16, 8038-8041

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    Catalyst-free 1 : 2 annulation of quinolines with trifluoroacetylacetylenes: an access to functionalized oxazinoquinolines

    K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko, V. M. Muzalevskiy, V. G. Nenajdenko and B. A. Trofimov, Org. Biomol. Chem., 2018, 16, 8038
    DOI: 10.1039/C8OB02379D

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