Issue 18, 2018

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

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

Supplementary files

Article information

Article type
Communication
Submitted
20 Dec 2017
Accepted
29 Jan 2018
First published
29 Jan 2018

Chem. Commun., 2018,54, 2268-2271

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, 54, 2268 DOI: 10.1039/C7CC09725E

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