α,β-Disubstituted CF3-Enones as a Trifluoromethyl Building Block: Regioselective Preparation of Totally Substituted 3-CF3-Pyrazoles
Publication type: Journal Article
Publication date: 2021-01-11
scimago Q2
wos Q1
SJR: 0.737
CiteScore: 6.1
Impact factor: 3.6
ISSN: 00223263, 15206904
PubMed ID:
33423495
Organic Chemistry
Abstract
An efficient pathway toward a novel class of trifluoromethyl building blocks was elaborated. The reaction of α-CF3-enamines with arylaldehydes resulted in direct synthesis of α,β-diaryl-CF3-enones isolated in up to 93% yield as E-isomers. The possible reaction mechanism was proposed using the Zimmerman-Traxler model. The reaction of α,β-diaryl-CF3-enones with hydrazines opens a novel pathway to trifluoromethylated pyrazolines. Oxidation of pyrazolines with DDQ opened access to totally regioselective preparation of 3-CF3-pyrazoles isolated in high yield. Using this strategy, 4-arylated derivatives of known drugs Celebrex, Mavacoxib, and SC-560 can be synthesized.
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Total citations:
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GOST
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Muzalevskiy V. M. et al. α,β-Disubstituted CF3-Enones as a Trifluoromethyl Building Block: Regioselective Preparation of Totally Substituted 3-CF3-Pyrazoles // Journal of Organic Chemistry. 2021. Vol. 86. No. 3. pp. 2385-2405.
GOST all authors (up to 50)
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Muzalevskiy V. M., Sizova Z. A., Panyushkin V. V., Chertkov V. A., Khrustalev V. N., Nenajdenko V. G. α,β-Disubstituted CF3-Enones as a Trifluoromethyl Building Block: Regioselective Preparation of Totally Substituted 3-CF3-Pyrazoles // Journal of Organic Chemistry. 2021. Vol. 86. No. 3. pp. 2385-2405.
Cite this
RIS
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TY - JOUR
DO - 10.1021/acs.joc.0c02516
UR - https://doi.org/10.1021/acs.joc.0c02516
TI - α,β-Disubstituted CF3-Enones as a Trifluoromethyl Building Block: Regioselective Preparation of Totally Substituted 3-CF3-Pyrazoles
T2 - Journal of Organic Chemistry
AU - Muzalevskiy, Vasily M.
AU - Sizova, Zoia A
AU - Panyushkin, Vasiliy V
AU - Chertkov, Vyacheslav A.
AU - Khrustalev, Victor N.
AU - Nenajdenko, Valentine G.
PY - 2021
DA - 2021/01/11
PB - American Chemical Society (ACS)
SP - 2385-2405
IS - 3
VL - 86
PMID - 33423495
SN - 0022-3263
SN - 1520-6904
ER -
Cite this
BibTex (up to 50 authors)
Copy
@article{2021_Muzalevskiy,
author = {Vasily M. Muzalevskiy and Zoia A Sizova and Vasiliy V Panyushkin and Vyacheslav A. Chertkov and Victor N. Khrustalev and Valentine G. Nenajdenko},
title = {α,β-Disubstituted CF3-Enones as a Trifluoromethyl Building Block: Regioselective Preparation of Totally Substituted 3-CF3-Pyrazoles},
journal = {Journal of Organic Chemistry},
year = {2021},
volume = {86},
publisher = {American Chemical Society (ACS)},
month = {jan},
url = {https://doi.org/10.1021/acs.joc.0c02516},
number = {3},
pages = {2385--2405},
doi = {10.1021/acs.joc.0c02516}
}
Cite this
MLA
Copy
Muzalevskiy, Vasily M., et al. “α,β-Disubstituted CF3-Enones as a Trifluoromethyl Building Block: Regioselective Preparation of Totally Substituted 3-CF3-Pyrazoles.” Journal of Organic Chemistry, vol. 86, no. 3, Jan. 2021, pp. 2385-2405. https://doi.org/10.1021/acs.joc.0c02516.