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Unexpected transformation of 3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one into 2,6-diphenyl-4-trifluoromethylpyridine

Vera Ivanovna Filyakova 1
Vera Ivanovna Filyakova
, 
Nadezhda S Boltacheva 1
Nadezhda S Boltacheva
, 
Pavel Alexandrovich Slepukhin 1, 2
Pavel Alexandrovich Slepukhin
, 
Marina Gennadievna Pervova 1
Marina Gennadievna Pervova
, 
Valery Nikolaevich Charushin 1, 2
Valery Nikolaevich Charushin
10.1016/j.mencom.2020.09.042
Published 2020-08-31
Communication , Volume 30, Issue 5, 676-678
5
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Filyakova V. I. et al. Unexpected transformation of 3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one into 2,6-diphenyl-4-trifluoromethylpyridine // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 676-678.
GOST all authors (up to 50) Copy
Filyakova V. I., Boltacheva N. S., Slepukhin P. A., Pervova M. G., Charushin V. N. Unexpected transformation of 3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one into 2,6-diphenyl-4-trifluoromethylpyridine // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 676-678.
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TY - JOUR
DO - 10.1016/j.mencom.2020.09.042
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.042
TI - Unexpected transformation of 3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one into 2,6-diphenyl-4-trifluoromethylpyridine
T2 - Mendeleev Communications
AU - Filyakova, Vera Ivanovna
AU - Boltacheva, Nadezhda S
AU - Slepukhin, Pavel Alexandrovich
AU - Pervova, Marina Gennadievna
AU - Charushin, Valery Nikolaevich
PY - 2020
DA - 2020/08/31
PB - Mendeleev Communications
SP - 676-678
IS - 5
VL - 30
ER -
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@article{2020_Filyakova,
author = {Vera Ivanovna Filyakova and Nadezhda S Boltacheva and Pavel Alexandrovich Slepukhin and Marina Gennadievna Pervova and Valery Nikolaevich Charushin},
title = {Unexpected transformation of 3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one into 2,6-diphenyl-4-trifluoromethylpyridine},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.042},
number = {5},
pages = {676--678},
doi = {10.1016/j.mencom.2020.09.042}
}
MLA
Cite this
MLA Copy
Filyakova, Vera Ivanovna, et al. “Unexpected transformation of 3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one into 2,6-diphenyl-4-trifluoromethylpyridine.” Mendeleev Communications, vol. 30, no. 5, Aug. 2020, pp. 676-678. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.042.

Keywords

heterocyclization
organofluorine compounds
pyridines
regioisomerism
β-aminovinyl ketones

Abstract

On heating in glacial acetic acid (or ethanol in the presence of manganese(ii) acetate), 3-amino-4,4,4-trifluoro-1-phenylbut-2-en-1-one undergoes unusual transformation into 2,6-diphenyl-4-trifluoromethylpyridine. The regioisomeric β-aminovinyl ketone, viz. 1-amino-4,4,4-trifluoro-1-phenylbut-1-en-3-one, remains unchanged under similar reaction conditions.

References

1.
Recent advances in the chemistry of α,β-unsaturated trifluoromethylketones
Druzhinin S.V., Balenkova E.S., Nenajdenko V.G.
Tetrahedron, 2007
2.
Efficient and convenient entry to β-hydroxy-β-trifluoromethyl-β-substituted ketones and 2,6-disubstituted 4-trifluoromethylpyridines based on the reaction of trifluoromethyl ketones with enamines or imines
Funabiki K., Isomura A., Yamaguchi Y., Hashimoto W., Matsunaga K., Shibata K., Matsui M.
Journal of the Chemical Society Perkin Transactions 1, 2001
6.
Polyfluoro- and perfluoroalkoxyenaminones in syntheses of nitrogen containing heterocycles
Davydova Y.A., Sokolenko T.M., Yagupolskii Y.L.
Journal of Fluorine Chemistry, 2014
9.
Synthesis, structure and ethylene polymerization behavior of zirconium complexes with chelating ketoiminate ligands
Kim J., Hwang J., Kim Y., Hyung Lee M., Han Y., Do Y.
Journal of Organometallic Chemistry, 2001
10.
Chelates of fluoroalkyl containing enaminoketones
Filyakova V.I., Chizhov D.L., Khmara E.F., Charushin V.N.
Russian Journal of General Chemistry, 2010
11.
Quenching of Fluorescence in Bodipy‐Derived Trifluoromethyl Enaminone Ligands upon Coordination to Copper(II)
Chopin N., Médebielle M., Maury O., Novitchi G., Pilet G.
European Journal of Inorganic Chemistry, 2014
12.
Copper(II) Cubane Complexes Built from Electro‐ and Photosensitive β‐Aminovinyl Trifluoromethyl Ketone Ligands
Chopin N., Chastanet G., Le Guennic B., Médebielle M., Pilet G.
European Journal of Inorganic Chemistry, 2012
16.
Structure and thermal properties of a novel volatile bis(1,1,1-trifluoro-5,5-dimethyl-3-hexene-4-imino-2-onate) platinum(II) compound
Zharkova G.I., Baidina I.A., Smolentsev A.I., Stabnikov P.A., Morozova N.B.
Journal of Structural Chemistry, 2017
17.
Synthesis and crystal structure of 1,1,1,5,5,5-hexafluoro-2-aminopentan-4-one (HFAP)
Johnson D.A., Waugh A.B., Hambley T.W., Taylor J.C.
Journal of Fluorine Chemistry, 1985
18.
Interaction of fluoroalkyl-containing ?-diketones with amines
Filyakova V.I., Ratner Y.G., Karpenko N.S., Pashkevich K.I.
Russian Chemical Bulletin, 1996
19.
10.1016/j.mencom.2020.09.042_bib0095
Karpenko
Russ. J. Org. Chem., 1997
21.
Fluoroalkyl-Containing Lithium 1,3-Diketonates in Reactions with Amines and Ammonium Salts
Boltacheva N.S., Filyakova V.I., Charushin V.N.
Russian Journal of Organic Chemistry, 2005
22.
A new perfluoromethyl aminoenone derivative and the role of the hydrogen bonding in the intra- and intermolecular interactions
Rocha M., Gil D.M., Echeverría G.A., Piro O.E., Jios J.L., Ulic S.E.
Journal of Fluorine Chemistry, 2018
23.
O-N, S-N and N-N exchange reactions at olefinic carbon atoms: Facile synthetic method for β-trifluoroacetylvinylamines
Hojo M., Masuda R., Okada E., Sakaguchi S., Narumiya H., Morimoto K.
Tetrahedron Letters, 1989
24.
Isomerization of fluorine-containing ?-aminovinyl ketones
Filyakova V.I., Pashkevich K.I., Postovskii I.Y.
Russian Chemical Bulletin, 1981
25.
10.1016/j.mencom.2020.09.042_bib0125
Filyakova
J. Org. Chem. USSR (Engl. Transl.), 1989
27.
Exchange reaction between fluorine-containing ?-diketones and ?-aminovinylketones
Filyakova V.I., Pashkevich K.I.
Russian Chemical Bulletin, 1989
28.
10.1016/j.mencom.2020.09.042_bib0140
2014
29.
Organofluorine chemistry: promising growth areas and challenges
Politanskaya L.V., Selivanova G.A., Panteleeva E.V., Tretyakov E.V., Platonov V.E., Nikul’shin P.V., Vinogradov A.S., Zonov Y.V., Karpov V.M., Mezhenkova T.V., Vasilyev A.V., Koldobskii A.B., Shilova O.S., Morozova S.M., Burgart Y.V., et. al.
Russian Chemical Reviews, 2019