Heterocycles Based on Bis(trifluoromethyl)imidazolidin-2-ones, 2-Aminoethanol, and 2-Aminophenol

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Heterocycles Based on Bis(trifluoromethyl)imidazolidin-2-ones, 2-Aminoethanol, and 2-Aminophenol. / Saloutina, L.; Kodess, M.; Ganebnykh, I. et al.
In: Russian Journal of Organic Chemistry, Vol. 59, No. 4, 01.04.2023, p. 623-630.

Research output: Contribution to journal › Article › peer-review

Author

Saloutina, L. ; Kodess, M. ; Ganebnykh, I. et al. / Heterocycles Based on Bis(trifluoromethyl)imidazolidin-2-ones, 2-Aminoethanol, and 2-Aminophenol. In: Russian Journal of Organic Chemistry. 2023 ; Vol. 59, No. 4. pp. 623-630.

BibTeX

@article{8bcdf465896549adbfac1dcf8b2f001f,

title = "Heterocycles Based on Bis(trifluoromethyl)imidazolidin-2-ones, 2-Aminoethanol, and 2-Aminophenol",

abstract = "New trifluoromethyl-substituted imidazo[4,5-b][1,4]oxazines were synthesized by the condensation of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one with 2-aminoethanol and 2-aminophenol. An unusual pathway was observed in the reactions of 1-methyl- and 1-phenyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones with 2-aminoethanol, which led to the formation of 5-[(2-hydroxyethyl)amino]-3-methyl(phenyl)hydantoins. 1-Methyl- and 1-phenyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones reacted with 2-aminophenol under similar conditions to give rearrangement products, 5,5-bis(trifluoromethyl)hydantoins. The molecular structure of 5-[(2-hydroxyethyl)amino]-3-methyl-5-(trifluoromethyl)imidazolidine-2,4-dione was determined by X-ray analysis.",

author = "L. Saloutina and M. Kodess and I. Ganebnykh and P. Slepukhin and V. Saloutin and O. Chupakhin",

note = "The spectral and analytical studies were performed using the facilities of the Spectroscopy and Analysis of Organic Compounds joint center at the Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences. This study was financially supported by the Ministry of Science and Higher Education (project no. AAAA-A19119011790132-7).",

year = "2023",

month = apr,

day = "1",

doi = "10.1134/S1070428023040097",

language = "English",

volume = "59",

pages = "623--630",

journal = "Russian Journal of Organic Chemistry",

issn = "1070-4280",

publisher = "Maik Nauka-Interperiodica Publishing",

number = "4",

}

RIS

TY - JOUR

T1 - Heterocycles Based on Bis(trifluoromethyl)imidazolidin-2-ones, 2-Aminoethanol, and 2-Aminophenol

AU - Saloutina, L.

AU - Kodess, M.

AU - Ganebnykh, I.

AU - Slepukhin, P.

AU - Saloutin, V.

AU - Chupakhin, O.

N1 - The spectral and analytical studies were performed using the facilities of the Spectroscopy and Analysis of Organic Compounds joint center at the Postovsky Institute of Organic Synthesis, Ural Branch, Russian Academy of Sciences. This study was financially supported by the Ministry of Science and Higher Education (project no. AAAA-A19119011790132-7).

PY - 2023/4/1

Y1 - 2023/4/1

N2 - New trifluoromethyl-substituted imidazo[4,5-b][1,4]oxazines were synthesized by the condensation of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one with 2-aminoethanol and 2-aminophenol. An unusual pathway was observed in the reactions of 1-methyl- and 1-phenyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones with 2-aminoethanol, which led to the formation of 5-[(2-hydroxyethyl)amino]-3-methyl(phenyl)hydantoins. 1-Methyl- and 1-phenyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones reacted with 2-aminophenol under similar conditions to give rearrangement products, 5,5-bis(trifluoromethyl)hydantoins. The molecular structure of 5-[(2-hydroxyethyl)amino]-3-methyl-5-(trifluoromethyl)imidazolidine-2,4-dione was determined by X-ray analysis.

AB - New trifluoromethyl-substituted imidazo[4,5-b][1,4]oxazines were synthesized by the condensation of 4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-one with 2-aminoethanol and 2-aminophenol. An unusual pathway was observed in the reactions of 1-methyl- and 1-phenyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones with 2-aminoethanol, which led to the formation of 5-[(2-hydroxyethyl)amino]-3-methyl(phenyl)hydantoins. 1-Methyl- and 1-phenyl-4,5-dihydroxy-4,5-bis(trifluoromethyl)imidazolidin-2-ones reacted with 2-aminophenol under similar conditions to give rearrangement products, 5,5-bis(trifluoromethyl)hydantoins. The molecular structure of 5-[(2-hydroxyethyl)amino]-3-methyl-5-(trifluoromethyl)imidazolidine-2,4-dione was determined by X-ray analysis.

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UR - https://gateway.webofknowledge.com/gateway/Gateway.cgi?GWVersion=2&SrcAuth=tsmetrics&SrcApp=tsm_test&DestApp=WOS_CPL&DestLinkType=FullRecord&KeyUT=001018571500009

U2 - 10.1134/S1070428023040097

DO - 10.1134/S1070428023040097

M3 - Article

VL - 59

SP - 623

EP - 630

JO - Russian Journal of Organic Chemistry

JF - Russian Journal of Organic Chemistry

SN - 1070-4280

IS - 4

ER -

ID: 41593662