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

Author:

Trofimov B. A.123ORCID,Belyaeva K. V.123,Nikitina L. P.123,Afonin A. V.123,Vashchenko A. V.123,Muzalevskiy V. M.453,Nenajdenko V. G.453

Affiliation:

1. A. E. Favorsky Irkutsk Institute of Chemistry, Siberian Branch, Russian Academy of Sciences

2. Irkutsk

3. Russian Federation

4. M. V. Lomonosov Moscow State University, Department of Chemistry

5. Moscow

Abstract

Metal-free reaction between quinolines, aryltrifluoroacetylacetylenes and water resulted in stereoselective assembly of trifluoromethylated oxazinoquinolines with up to 99% yield.

Publisher

Royal Society of Chemistry (RSC)

Subject

Materials Chemistry,Metals and Alloys,Surfaces, Coatings and Films,General Chemistry,Ceramics and Composites,Electronic, Optical and Magnetic Materials,Catalysis

Reference21 articles.

1. Ring-Opening of Pyridines with Acyl­acetylenes and Water: Straightforward Access to 5-[(Z)-Acylethenyl]amino-2,4-pentadienals

2. Opening of the pyridine ring in the system 1,1,1-trifluoro-4-phenylbut-3-yn-2-one–water. Stereoselective synthesis of 5-{[(1Z)-4,4,4-trifluoro-3-oxo-1-phenylbut-1-en-1-yl]amino}penta-2,4-dienal

3. H. C. Brown , D. H.McDaniel and O.Hafliger , Dissociation Constants , in Determination of Organic Structures by Physical Methods , ed. E. A. Braude and F. C. Nachod , Academic Press , 1955 , vol. 1, pp. 567–662

4. Recent advances in the design and synthesis of heterocycles as anti-tubercular agents

5. Fluorine in Heterocyclic Chemistry , ed. V. G. Nenajdenko , Springer International Publishing , Switzerland , 2014 , vol. 1–2

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