The competitive N1-, N2-, O- and C-methylation of 3-trifluoromethyl-1H-pyrazol-5-ol for synthesis of analgesic compounds
Ya. V. Burgart
1
,
N A Agafonova
1
,
Vera V Maslova
3
,
S Yu Solodnikov
3
,
O P Krasnykh
3
,
V. I. Saloutin
1
2
Publication type: Journal Article
Publication date: 2019-02-01
scimago Q3
wos Q3
SJR: 0.333
CiteScore: 3.7
Impact factor: 1.9
ISSN: 00221139, 18733328
Organic Chemistry
Biochemistry
Inorganic Chemistry
Physical and Theoretical Chemistry
Environmental Chemistry
Abstract
We have found selective conditions for methylation of 3-trifluoromethyl-1H-pyrazol-5-ol that allowed us to obtain mono-Me-substituted N1- and O-isomers as well N1,N2-, N1,O- and N2,O-disubstituted isomers. A tautomeric structure of the parent pyrazole and its Me-substituted derivatives was investigated using quantum-chemical calculations, X-ray diffraction analysis, IR and NMR spectroscopy. Besides, the quantum-chemical calculations were used to explain the methylation direction. An analgesic activity and acute toxicity of some synthesized compounds were evaluated in vivo experiments.
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11
Total citations:
11
Citations from 2024:
2
(18.18%)
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Burgart Y. V. et al. The competitive N1-, N2-, O- and C-methylation of 3-trifluoromethyl-1H-pyrazol-5-ol for synthesis of analgesic compounds // Journal of Fluorine Chemistry. 2019. Vol. 218. pp. 1-10.
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Burgart Y. V., Agafonova N. A., Shchegol’kov E., Borisevich S. S., Khursan S. L., Maslova V. V., Triandafilova G. A., Solodnikov S. Yu., Krasnykh O. P., Saloutin V. I. The competitive N1-, N2-, O- and C-methylation of 3-trifluoromethyl-1H-pyrazol-5-ol for synthesis of analgesic compounds // Journal of Fluorine Chemistry. 2019. Vol. 218. pp. 1-10.
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TY - JOUR
DO - 10.1016/j.jfluchem.2018.11.009
UR - https://linkinghub.elsevier.com/retrieve/pii/S0022113918304639
TI - The competitive N1-, N2-, O- and C-methylation of 3-trifluoromethyl-1H-pyrazol-5-ol for synthesis of analgesic compounds
T2 - Journal of Fluorine Chemistry
AU - Burgart, Ya. V.
AU - Agafonova, N A
AU - Shchegol’kov, E.V.
AU - Borisevich, Sophia S.
AU - Khursan, Sergey L.
AU - Maslova, Vera V
AU - Triandafilova, Galina A
AU - Solodnikov, S Yu
AU - Krasnykh, O P
AU - Saloutin, V. I.
PY - 2019
DA - 2019/02/01
PB - Elsevier
SP - 1-10
VL - 218
SN - 0022-1139
SN - 1873-3328
ER -
Cite this
BibTex (up to 50 authors)
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@article{2019_Burgart,
author = {Ya. V. Burgart and N A Agafonova and E.V. Shchegol’kov and Sophia S. Borisevich and Sergey L. Khursan and Vera V Maslova and Galina A Triandafilova and S Yu Solodnikov and O P Krasnykh and V. I. Saloutin},
title = {The competitive N1-, N2-, O- and C-methylation of 3-trifluoromethyl-1H-pyrazol-5-ol for synthesis of analgesic compounds},
journal = {Journal of Fluorine Chemistry},
year = {2019},
volume = {218},
publisher = {Elsevier},
month = {feb},
url = {https://linkinghub.elsevier.com/retrieve/pii/S0022113918304639},
pages = {1--10},
doi = {10.1016/j.jfluchem.2018.11.009}
}