Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones
Marina V. Goryaeva
1, 2, 3, 4, 5
,
Svetlana O Kushch
1, 2, 3, 4, 5
,
O.G. Khudina
1, 2, 3, 4, 5
,
Yanina V. Burgart
1, 2, 3, 4, 5
,
Yulia S Kudyakova
1, 2, 3, 4, 5
,
Marina A Ezhikova
1, 2, 3, 4, 5
,
Mikhail I. Kodess
1, 2, 3, 4, 5
,
Pavel A. Slepukhin
1, 2, 3, 4, 5
,
Lilya Sh Sadretdinova
1, 2, 3, 4, 5
,
Natalya P Evstigneeva
5, 6, 7, 8
,
Natalya A Gerasimova
5, 6, 7, 8
,
Victor Saloutin
1, 2, 3, 4, 5
2
Ural Branch
3
RUSSIAN ACADEMY OF SCIENCES
4
620990 Ekaterinburg
|
5
Russia
|
6
Ural Research Institute for Dermatology
7
Venereology and Immunopathology
8
620076 Ekaterinburg
|
Publication type: Journal Article
Publication date: 2019-03-26
scimago Q2
wos Q2
SJR: 0.600
CiteScore: 5.2
Impact factor: 2.7
ISSN: 14770520, 14770539
PubMed ID:
30938405
Organic Chemistry
Biochemistry
Physical and Theoretical Chemistry
Abstract
A new one-pot reaction between polyfluoroalkylated 3-oxo esters, methyl ketones and primary or secondary alkyl amines is reported as an efficient approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones. The scope of three-component cyclization and its plausible mechanism are discussed. The described protocol makes it possible to vary the functional substituents in 2, 3 and 5 positions of carbocycles. Anhydrous conditions are necessary for the productive synthesis of aminocyclohexenones, whereas in the presence of water the competitive formation of alkyl ammonium salts of keto hydroxy carboxylates is observed. Dehydration of the aminocyclohexenones was effectively used for the synthesis of 3-alkylamino-5-trifluoromethylphenols, some of which exhibited moderate antifungal activities against eight pathogenic fungal strains.
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Total citations:
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Citations from 2025:
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(14.29%)
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Goryaeva M. V. et al. Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones // Organic and Biomolecular Chemistry. 2019. Vol. 17. No. 17. pp. 4273-4280.
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Goryaeva M. V. et al. Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones // Organic and Biomolecular Chemistry. 2019. Vol. 17. No. 17. pp. 4273-4280.
Cite this
RIS
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TY - JOUR
DO - 10.1039/c9ob00293f
UR - https://xlink.rsc.org/?DOI=C9OB00293F
TI - Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones
T2 - Organic and Biomolecular Chemistry
AU - Goryaeva, Marina V.
AU - Kushch, Svetlana O
AU - Khudina, O.G.
AU - Burgart, Yanina V.
AU - Kudyakova, Yulia S
AU - Ezhikova, Marina A
AU - Kodess, Mikhail I.
AU - Slepukhin, Pavel A.
AU - Sadretdinova, Lilya Sh
AU - Evstigneeva, Natalya P
AU - Gerasimova, Natalya A
AU - Saloutin, Victor
PY - 2019
DA - 2019/03/26
PB - Royal Society of Chemistry (RSC)
SP - 4273-4280
IS - 17
VL - 17
PMID - 30938405
SN - 1477-0520
SN - 1477-0539
ER -
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BibTex (up to 50 authors)
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@article{2019_Goryaeva,
author = {Marina V. Goryaeva and Svetlana O Kushch and O.G. Khudina and Yanina V. Burgart and Yulia S Kudyakova and Marina A Ezhikova and Mikhail I. Kodess and Pavel A. Slepukhin and Lilya Sh Sadretdinova and Natalya P Evstigneeva and Natalya A Gerasimova and Victor Saloutin and others},
title = {Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones},
journal = {Organic and Biomolecular Chemistry},
year = {2019},
volume = {17},
publisher = {Royal Society of Chemistry (RSC)},
month = {mar},
url = {https://xlink.rsc.org/?DOI=C9OB00293F},
number = {17},
pages = {4273--4280},
doi = {10.1039/c9ob00293f}
}
Cite this
MLA
Copy
Goryaeva, Marina V., et al. “Autocatalyzed three-component cyclization of polyfluoroalkyl-3-oxo esters, methyl ketones and alkyl amines: a novel approach to 3-alkylamino-5-hydroxy-5-polyfluoroalkylcyclohex-2-en-1-ones.” Organic and Biomolecular Chemistry, vol. 17, no. 17, Mar. 2019, pp. 4273-4280. https://xlink.rsc.org/?DOI=C9OB00293F.