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Metal-free stereoselective annulation of quinolines with trifluoroacetylacetylenes and water: an access to fluorinated oxazinoquinolines

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Abstract

Metal-free reaction between quinolines, aryltrifluoroacetylacetylenes and water at −18 °C–rt in MeCN resulted in stereoselective assembly of trifluoromethylated oxazinoquinolines with up to 99% yield that was essentially in contrast to a similar reaction with pyridines. The annulation proceeded via the 1,3-dipolar adducts of quinolines with trifluoroacetylacetylenes followed by intramolecular cyclization involving the trifluoroacetyl group and a molecule of water.

Graphical abstract: Metal-free stereoselective annulation of quinolines with trifluoroacetylacetylenes and water: an access to fluorinated oxazinoquinolines

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Publication details

The article was received on 20 Dec 2017, accepted on 29 Jan 2018 and first published on 29 Jan 2018


Article type: Communication
DOI: 10.1039/C7CC09725E
Citation: Chem. Commun., 2018, Advance Article
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    Metal-free stereoselective annulation of quinolines with trifluoroacetylacetylenes and water: an access to fluorinated oxazinoquinolines

    B. A. Trofimov, K. V. Belyaeva, L. P. Nikitina, A. V. Afonin, A. V. Vashchenko, V. M. Muzalevskiy and V. G. Nenajdenko, Chem. Commun., 2018, Advance Article , DOI: 10.1039/C7CC09725E

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