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

Andriyankova, L. V.; Никитина, Л. П.; Belyaeva, Kseniya V.; Малькина, А. Г.; Afonin, A. V.; Музалевский, В. M.; Nenaidenko, V. G.; Трофимов, Б. А.

doi:10.1134/s1070428016120289

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Cited by 10 publications

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“…The reaction of pyridine with equal amount of CF 3 -ynone in wet acetonitrile afforded the corresponding ring opening product. Polyunsaturated 5-amino-2,4-pentadienal 7 has been isolated as a result of cascade transformation (Scheme 1) [57].…”

Section: Introductionmentioning

confidence: 99%

One-Pot Metal-Free Synthesis of 3-CF3-1,3-Oxazinopyridines by Reaction of Pyridines with CF3CO-Acetylenes

et al. 2019

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The reaction of pyridines with trifluoroacetylated acetylenes was investigated. It was found that the reaction of various pyridines with two molecules of CF3CO-acetylenes proceeds under mild metal-free conditions. As a result, efficient stereoselective synthesis of 3-arylethynyl-3-trifluoromethyl-1,3-oxazinopyridines was elaborated. Target heterocycles can be prepared in up to quantitative yields.

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Section: Introductionmentioning

confidence: 99%

One-Pot Metal-Free Synthesis of 3-CF3-1,3-Oxazinopyridines by Reaction of Pyridines with CF3CO-Acetylenes

et al. 2019

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Uniquely functionalized tetrahydropyrido[2,1-b][1,3]oxazines: Diastereoselective 1:2 assembly from pyridines with oxalylacetylenes

Belyaeva

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Никитина

et al. 2021

Tetrahedron Letters

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

et al. 2018

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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 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.

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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

Cited by 10 publications

References 20 publications

One-Pot Metal-Free Synthesis of 3-CF3-1,3-Oxazinopyridines by Reaction of Pyridines with CF3CO-Acetylenes

One-Pot Metal-Free Synthesis of 3-CF3-1,3-Oxazinopyridines by Reaction of Pyridines with CF3CO-Acetylenes

Uniquely functionalized tetrahydropyrido[2,1-b][1,3]oxazines: Diastereoselective 1:2 assembly from pyridines with oxalylacetylenes

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

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