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

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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… Click to show full 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.

Keywords: quinolines trifluoroacetylacetylenes; water; free stereoselective; stereoselective annulation; metal free

Journal Title: Chemical communications
Year Published: 2018

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