- Acetylene-free synthesis of vinyloxy pyridine and quinoline
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Copper-catalyzed vinylation of 2- and 4-hydroxy pyridine and quinoline affords exclusively N-vinylation products. However, vinyl ethers of 4-hydroxy pyridine and quinoline can be prepared via a three-step sequence involving copper-catalyzed C-O cross coupling reaction of the corresponding N-heteroaryl bromides with ethylene glycol, chlorination of the terminal alcohol, and dehydrohalogenation of the β-chloro ethers. Although not efficient in 2-hydroxy series, this method can be conveniently applied to the preparation of various aza-aryl vinyl ethers in moderate to good overall yields.
- Hamdi, Abdelrahman,Mostafa, Amany S.,Watat, Cedric Nana,Laurent, Mathieu Y.,Ben Ayed, Kawther,Selim, Khalid B.,Dujardin, Gilles
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supporting information
p. 5825 - 5829
(2016/12/06)
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- STRUCTURE OF 1-VINYL-2- AND 1-VINYL-4-PYRIDONES (QUINOLONES) ACCORDING TO 1H AND 13C NMR DATA
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1-Vinyl-2-pyridone, 1-vinyl-4-pyridone, 1-vinyl-2-quinolone, 1-vinyl-4-methyl-2-quinolone, 1-vinyl-4-quinolone, and 1-vinyl-2-methyl-4-quinolone were obtained by the direct vinylation of the corresponding pyridones and quinolones.The sterechemical orientation of the vinyl group in these compounds was established by 1H and 13C NMR spectroscopy.The vinyl derivatives of 2- and 4-pyridones and also 4-quinolone are characterized by a coplanar arrangement of the vinyl group and the heterocycle with the preferred trans orientation in relation to the substituent at the ortho position.In 1-vinyl-2- quinolones and 1-vinyl-2-methyl-4-quinolone the vinyl group and heterocyclic fragment are not coplanar.
- Afonin, A. V.,Andriyankov, M. A.,Pertsikov, B. Z.,Voronov, V. K.
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p. 2202 - 2204
(2007/10/02)
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