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Step by step and one-pot syntheses of 5-hydroxy-5-(polyfluoroalkyl)isoxazol-4(5H)-one oximes

Nadezhda Vladimirovna Palysaeva 1
Nadezhda Vladimirovna Palysaeva
, 
Nadezhda S Boltacheva 2
Nadezhda S Boltacheva
, 
Pavel Alexandrovich Slepukhin 2
Pavel Alexandrovich Slepukhin
, 
Marina Gennadievna Pervova 2
Marina Gennadievna Pervova
, 
Vera Ivanovna Filyakova 2
Vera Ivanovna Filyakova
, 
Aleksei Borisovich Sheremetev 1
Aleksei Borisovich Sheremetev
, 
Valery Nikolaevich Charushin 2, 3
Valery Nikolaevich Charushin
10.1016/j.mencom.2018.03.003
Published 2018-03-01
Communication , Volume 28, Issue 2, 126-127
8
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Palysaeva N. V. et al. Step by step and one-pot syntheses of 5-hydroxy-5-(polyfluoroalkyl)isoxazol-4(5H)-one oximes // Mendeleev Communications. 2018. Vol. 28. No. 2. pp. 126-127.
GOST all authors (up to 50) Copy
Palysaeva N. V., Boltacheva N. S., Slepukhin P. A., Pervova M. G., Filyakova V. I., Sheremetev A. B., Charushin V. N. Step by step and one-pot syntheses of 5-hydroxy-5-(polyfluoroalkyl)isoxazol-4(5H)-one oximes // Mendeleev Communications. 2018. Vol. 28. No. 2. pp. 126-127.
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TY - JOUR
DO - 10.1016/j.mencom.2018.03.003
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.03.003
TI - Step by step and one-pot syntheses of 5-hydroxy-5-(polyfluoroalkyl)isoxazol-4(5H)-one oximes
T2 - Mendeleev Communications
AU - Palysaeva, Nadezhda Vladimirovna
AU - Boltacheva, Nadezhda S
AU - Slepukhin, Pavel Alexandrovich
AU - Pervova, Marina Gennadievna
AU - Filyakova, Vera Ivanovna
AU - Sheremetev, Aleksei Borisovich
AU - Charushin, Valery Nikolaevich
PY - 2018
DA - 2018/03/01
PB - Mendeleev Communications
SP - 126-127
IS - 2
VL - 28
ER -
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@article{2018_Palysaeva,
author = {Nadezhda Vladimirovna Palysaeva and Nadezhda S Boltacheva and Pavel Alexandrovich Slepukhin and Marina Gennadievna Pervova and Vera Ivanovna Filyakova and Aleksei Borisovich Sheremetev and Valery Nikolaevich Charushin},
title = {Step by step and one-pot syntheses of 5-hydroxy-5-(polyfluoroalkyl)isoxazol-4(5H)-one oximes},
journal = {Mendeleev Communications},
year = {2018},
volume = {28},
publisher = {Mendeleev Communications},
month = {Mar},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.03.003},
number = {2},
pages = {126--127},
doi = {10.1016/j.mencom.2018.03.003}
}
MLA
Cite this
MLA Copy
Palysaeva, Nadezhda Vladimirovna, et al. “Step by step and one-pot syntheses of 5-hydroxy-5-(polyfluoroalkyl)isoxazol-4(5H)-one oximes.” Mendeleev Communications, vol. 28, no. 2, Mar. 2018, pp. 126-127. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2018.03.003.

Abstract

5-Hydroxy-5-(polyfluoroalkyl)isoxazol-4(5H)-one oximes have been obtained by nitrosation of lithium 3-polyfluoroalkyl-1,3-diketonates followed by treatment of intermediate 3-(poly-fluoroalkyl)propane-1,2,3-trione 2-oximes with hydroxylamine hydrochloride. The one-pot protocol comprising both stages has been elaborated.

References

1.
Isoxazole derivatives in the synthesis of bifunctional compounds by cleavage of the heteroring (review)
Akhrem A.A., Lakhvich F.A., Khripach V.A.
Chemistry of Heterocyclic Compounds, 1981
4.
Design, synthesis and cytotoxic activities of scopoletin-isoxazole and scopoletin-pyrazole hybrids
Shi W., Hu J., Bao N., Li D., Chen L., Sun J.
Bioorganic and Medicinal Chemistry Letters, 2017
7.
Synthesis and antioxidant activity of oxazolyl/thiazolylsulfonylmethyl pyrazoles and isoxazoles
Padmaja A., Rajasekhar C., Muralikrishna A., Padmavathi V.
European Journal of Medicinal Chemistry, 2011
8.
Reaction of naphthoquinones with substituted nitromethanes. Facile synthesis and antifungal activity of naphtho[2,3-d]isoxazole-4,9-diones.
Santos M.M., Faria N., Iley J., Coles S.J., Hursthouse M.B., Martins M.L., Moreira R.
Bioorganic and Medicinal Chemistry Letters, 2010
9.
4-[5-Methyl-3-phenylisoxazol-4-yl]- benzenesulfonamide, Valdecoxib:  A Potent and Selective Inhibitor of COX-2
Talley J.J., Brown D.L., Carter J.S., Graneto M.J., Koboldt C.M., Masferrer J.L., Perkins W.E., Rogers R.S., Shaffer A.F., Zhang Y.Y., Zweifel B.S., Seibert K.
Journal of Medicinal Chemistry, 2000
10.
Synthesis and biological evaluation of 3,5-diaryl isoxazoline/isoxazole linked 2,3-dihydroquinazolinone hybrids as anticancer agents.
Kamal A., Bharathi E.V., Reddy J.S., Ramaiah M.J., Dastagiri D., Reddy M.K., Viswanath A., Reddy T.L., Shaik T.B., Pushpavalli S.N., Bhadra M.P.
European Journal of Medicinal Chemistry, 2011
11.
Synthesis and antitumor activity of 2,5-bis(3′-indolyl)-furans and 3,5-bis(3′-indolyl)-isoxazoles, nortopsentin analogues
Diana P., Carbone A., Barraja P., Kelter G., Fiebig H., Cirrincione G.
Bioorganic and Medicinal Chemistry, 2010
12.
Fluorine Compounds. Synthesis and Application, ed. N. Ishikawa, Kodansha, Tokyo, 1986.
13.
10.1016/j.mencom.2018.03.003_bib0065
Kirsch
Modern Fluoroorganic Chemistry: Synthesis, Reactivity Applications, 2013
14.
Filyakova V.I., Boltachova N.S., Pervova M.G., Palysaeva N.V., Slepukhin P.A., Sheremetev A.B., Charushin V.N.
Mendeleev Communications, 2017
15.
Oximes as reagents
Mikhaleva A.I., Zaitsev A.B., Trofimov B.A.
Russian Chemical Reviews, 2006
16.
Oximation of acetyl(hydroxyimino)acetone: nuclear magnetic resonance spectroscopic, chemical, and X-ray crystallographic studies of the reaction products
Fruttero R., Calvino R., Ferrarotti B., Gasco A., Aime S., Gobetto R., Chiari G., Calestani G.
Journal of the Chemical Society Perkin Transactions 2, 1987
17.
Synthesis of oxadiazole-2-oxide analogues as potential antischistosomal agents
Rai G., Thomas C.J., Leister W., Maloney D.J.
Tetrahedron Letters, 2009
20.
Nitrosation of acetylacetone (pentane-2,4-dione) and some of its fluorinated derivatives
Crookes M.J., Roy P., Williams D.L.
Journal of the Chemical Society Perkin Transactions 2, 1989
21.
Synthesis of fluoroalkyl-containing 2-oxyimino-1,3-dicarbonyl compounds and their reaction with hydrazine hydrate
Saloutin V.I., Burgart Y.V., Skryabina Z.E., Kuzueva O.G.
Journal of Fluorine Chemistry, 1997
22.
10.1016/j.mencom.2018.03.003_bib0110
Lin-Vien
The Handbook of Infrared and Raman Characteristic Frequencies of Organic Molecules, 1991
24.
OLEX2: a complete structure solution, refinement and analysis program
Dolomanov O.V., Bourhis L.J., Gildea R.J., Howard J.A., Puschmann H.
Journal of Applied Crystallography, 2009
25.
A short history of SHELX
Sheldrick G.M.
Acta Crystallographica Section A Foundations of Crystallography, 2007
26.
10.1016/j.mencom.2018.03.003_bib0130
Bourhis
Acta Crystallogr., 2015