Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes
Vasily M. Muzalevskiy
1, 2, 3, 4, 5
,
Zoia A Sizova
1, 2, 3, 4, 5
,
Vladimir T. Abaev
5, 6, 7, 8, 9, 10, 11
,
Valentine G. Nenajdenko
1, 2, 3, 4, 5
2
DEPARTMENT OF CHEMISTRY
4
119899 Moscow
5
Russia
|
9
Vladikavkaz
|
11
Stavropol 355009
|
Publication type: Journal Article
Publication date: 2021-04-09
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
33899886
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
α-CF3-enamines can be prepared by the reaction of pyrrolidine with the corresponding haloalkenes. The prepared enamines react with 2-nitrobenzaldehydes to give ortho-nitro-substituted α,β-diaryl-CF3-enones highly stereoselectively in up to 88% yield. Subsequent reduction of the nitro-group by an Fe-AcOH system promotes intramolecular cyclization to afford 2-CF3-3-arylquinolines in up to 99% isolated yield. High synthetic utility of all synthetic steps of the sequence was shown. A one-pot procedure was developed to give the target trifluoromethylated quinolines directly from enamines or haloalkenes.
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13
Total citations:
13
Citations from 2024:
5
(38.46%)
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GOST
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Muzalevskiy V. M. et al. Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 19. pp. 4303-4319.
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Muzalevskiy V. M., Sizova Z. A., Abaev V. T., Nenajdenko V. G. Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes // Organic and Biomolecular Chemistry. 2021. Vol. 19. No. 19. pp. 4303-4319.
Cite this
RIS
Copy
TY - JOUR
DO - 10.1039/d1ob00098e
UR - https://xlink.rsc.org/?DOI=D1OB00098E
TI - Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes
T2 - Organic and Biomolecular Chemistry
AU - Muzalevskiy, Vasily M.
AU - Sizova, Zoia A
AU - Abaev, Vladimir T.
AU - Nenajdenko, Valentine G.
PY - 2021
DA - 2021/04/09
PB - Royal Society of Chemistry (RSC)
SP - 4303-4319
IS - 19
VL - 19
PMID - 33899886
SN - 1477-0520
SN - 1477-0539
ER -
Cite this
BibTex (up to 50 authors)
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@article{2021_Muzalevskiy,
author = {Vasily M. Muzalevskiy and Zoia A Sizova and Vladimir T. Abaev and Valentine G. Nenajdenko},
title = {Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes},
journal = {Organic and Biomolecular Chemistry},
year = {2021},
volume = {19},
publisher = {Royal Society of Chemistry (RSC)},
month = {apr},
url = {https://xlink.rsc.org/?DOI=D1OB00098E},
number = {19},
pages = {4303--4319},
doi = {10.1039/d1ob00098e}
}
Cite this
MLA
Copy
Muzalevskiy, Vasily M., et al. “Synthesis of 2-trifluoromethylated quinolines from CF3-alkenes.” Organic and Biomolecular Chemistry, vol. 19, no. 19, Apr. 2021, pp. 4303-4319. https://xlink.rsc.org/?DOI=D1OB00098E.