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Functionalization of 1,2-diphenylpyrazolidine-3,5-dione with polyfluoroalkyl-containing 2- and 3-oxo esters

Olga Georgievna Khudina 1
Olga Georgievna Khudina
, 
Yanina Valer'evna Burgart 1
Yanina Valer'evna Burgart
, 
Viktor Ivanovich Saloutin 1
Viktor Ivanovich Saloutin
10.1016/j.mencom.2020.09.026
Published 2020-08-31
Communication , Volume 30, Issue 5, 630-632
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Khudina O. G., Burgart Y. V., Saloutin V. I. Functionalization of 1,2-diphenylpyrazolidine-3,5-dione with polyfluoroalkyl-containing 2- and 3-oxo esters // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 630-632.
GOST all authors (up to 50) Copy
Khudina O. G., Burgart Y. V., Saloutin V. I. Functionalization of 1,2-diphenylpyrazolidine-3,5-dione with polyfluoroalkyl-containing 2- and 3-oxo esters // Mendeleev Communications. 2020. Vol. 30. No. 5. pp. 630-632.
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TY - JOUR
DO - 10.1016/j.mencom.2020.09.026
UR - https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.026
TI - Functionalization of 1,2-diphenylpyrazolidine-3,5-dione with polyfluoroalkyl-containing 2- and 3-oxo esters
T2 - Mendeleev Communications
AU - Khudina, Olga Georgievna
AU - Burgart, Yanina Valer'evna
AU - Saloutin, Viktor Ivanovich
PY - 2020
DA - 2020/08/31
PB - Mendeleev Communications
SP - 630-632
IS - 5
VL - 30
ER -
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@article{2020_Khudina,
author = {Olga Georgievna Khudina and Yanina Valer'evna Burgart and Viktor Ivanovich Saloutin},
title = {Functionalization of 1,2-diphenylpyrazolidine-3,5-dione with polyfluoroalkyl-containing 2- and 3-oxo esters},
journal = {Mendeleev Communications},
year = {2020},
volume = {30},
publisher = {Mendeleev Communications},
month = {Aug},
url = {https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.026},
number = {5},
pages = {630--632},
doi = {10.1016/j.mencom.2020.09.026}
}
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Khudina, Olga Georgievna, et al. “Functionalization of 1,2-diphenylpyrazolidine-3,5-dione with polyfluoroalkyl-containing 2- and 3-oxo esters.” Mendeleev Communications, vol. 30, no. 5, Aug. 2020, pp. 630-632. https://mendcomm.colab.ws/publications/10.1016/j.mencom.2020.09.026.

Keywords

1,2-diphenylpyrazolidine-3,5-dione
Knoevenagel reaction
non-steroidal anti-inflammatory drugs
polyfluoroalkyl 2-oxo esters
polyfluoroalkyl 3-oxo esters

Abstract

Fluorine-containing analogues of non-steroidal antiinflammatory drugs Tribuzone and Ketazone have been synthesized by reaction of 1,2-diphenylpyrazolidine-3,5-dione with polyfluoroalkyl-containing 3- and 2-oxo esters. Ethyl 3-(pyrazolidin-4-yl)-3-(polyfluoroalkyl)prop-2-enoates have been obtained as Knoevenagel reaction products from 3-oxo esters in the presence of l-proline. Unlike with 3-oxo esters, addition of ethyl 3,3,3-trifluoro-2-oxopropanoate under basic conditions afforded ethyl 2-(pyrazolidin-4-yl)-3,3,3-trifluoro-2-hydroxypropanoate or its salt without elimination of a water molecule.

References

2.
Flumizole, a New Nonsteroidal Anti‐Inflammatory Agent
McIlhenny H.M., Bettis J.W., Wiseman E.H.
Journal of Pharmaceutical Sciences, 1975
3.
G. G. Furin, Ftorsoderzhashchie geterotsiklicheskie soedineniya. Sintez i primenenie (Fluorinated Heterocyclic Compounds. Synthesis and Applications), Nauka, Novosibirsk, 2001.(in Russian).
4.
Synthesis and Biological Evaluation of the 1,5-Diarylpyrazole Class of Cyclooxygenase-2 Inhibitors:  Identification of 4-[5-(4-Methylphenyl)-3- (trifluoromethyl)-1H-pyrazol-1-yl]benzenesulfonamide (SC-58635, Celecoxib)
Penning T.D., Talley J.J., Bertenshaw S.R., Carter J.S., Collins P.W., Docter S., Graneto M.J., Lee L.F., Malecha J.W., Miyashiro J.M., Rogers R.S., Rogier D.J., Yu S.S., Anderson G.D., Burton E.G., et. al.
Journal of Medicinal Chemistry, 1997
5.
Silver-Mediated Cycloaddition of Alkynes with CF3CHN2: Highly Regioselective Synthesis of 3-Trifluoromethylpyrazoles
Li F., Nie J., Sun L., Zheng Y., Ma J.
Angewandte Chemie - International Edition, 2013
6.
The Many Roles for Fluorine in Medicinal Chemistry
Hagmann W.K.
Journal of Medicinal Chemistry, 2008
8.
The therapeutic voyage of pyrazole and its analogs: A review
Khan M.F., Alam M.M., Verma G., Akhtar W., Akhter M., Shaquiquzzaman M.
European Journal of Medicinal Chemistry, 2016
9.
Synthesis and Biological Evaluation of Polyfluoroalkylated Antipyrines and their Isomeric O-Methylpyrazoles
Agafonova N., Shchegolkov E., Burgart Y., Saloutin V., Trefilova A., Triandafilova G., Solodnikov S., Maslova V., Krasnykh O., Borisevich S., Khursan S.
Medicinal Chemistry, 2019
10.
The competitive N1-, N2-, O- and C-methylation of 3-trifluoromethyl-1H-pyrazol-5-ol for synthesis of analgesic compounds
Burgart Y.V., Agafonova N.A., Shchegolkov E.V., Borisevich S.S., Khursan S.L., Maslova V.V., Triandafilova G.A., Solodnikov S.Y., Krasnykh O.P., Saloutin V.I.
Journal of Fluorine Chemistry, 2019
11.
New one-pot synthesis of 4-hydroxyimino-5-polyfluoroalkylpyrazol-3-ones, their structure and biological activity
Burgart Y.V., Agafonova N.A., Shchegolkov E.V., Maslova V.V., Triandafilova G.A., Solodnikov S.Y., Krasnykh O.P., Saloutin V.I.
Chemistry of Heterocyclic Compounds, 2019
12.
Ivanova A.E., Burgart Y.V., Saloutin V.I., Orshanskaya Y.R., Zarubaev V.V.
Mendeleev Communications, 2018
13.
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
14.
Bazhin D.N., Kudyakova Y.S., Slepukhin P.A., Burgart Y.V., Malysheva N.N., Kozitsina A.N., Ivanova A.V., Bogomyakov A.S., Saloutin V.I.
Mendeleev Communications, 2018
15.
M. D. Mashkovskiy, Lekarstvennye sredstva (Pharmaceuticals), Novaya volna, Moscow, 2012.(in Russian).
16.
Lekarstvennye sredstva: svoistva, primenenie, protivopokazaniya (Pharmaceuticals: Properties, Applications, and Contraindications), ed. M. A. Klyuev, Russkaya kniga, Moscow, 1993.(in Russian).
17.
Synthesis of novel perfluoroalkyl-containing polyethers
Bazhin D.N., Gorbunova T.I., Zapevalov A.Y., Saloutin V.I.
Journal of Fluorine Chemistry, 2009
18.
10.1016/j.mencom.2020.09.026_bib0090
Organikum: Organisch-chemisches Grundpraktikum, 2004