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Multi-purpose thiocyanate protic ionic liquids in chemodivergent transformations of imidazolidin-2-(thi)one-based diols Full article

Journal Organic & Biomolecular Chemistry
ISSN: 1477-0520 , E-ISSN: 1477-0539
Output data Year: 2025, Volume: 23, Pages: 7157-7164 Pages count : 8 DOI: 10.1039/d5ob00709g
Authors Ermolaev Valery P. 1 , Ratmanova Nina K. 2 , Baranov Vladimir V. 3 , Levina Irina I. 4 , Khrustalev Victor N. 3,2 , Ivanova Olga A. 5 , Kravchenko Angelina N. 3 , Trushkov Igor V. 3 , Andreev Ivan A. 2
Affiliations
1 Higher Chemical College of the Russian Academy of Sciences, D. I. Mendeleev Russian University of Chemical Technology, Miusskaya Ploshchad’ 9, 125047 Moscow, Russian Federation
2 Science Faculty, Patrice Lumumba Peoples’ Friendship University of Russia (RUDN University), Miklukho-Maklaya st. 6, 117198 Moscow, Russian Federation
3 N. D. Zelinsky Institute of Organic Chemistry, Russian Academy of Sciences, Leninsky pr. 47, 119991 Moscow, Russian Federation
4 N. M. Emanuel Institute of Biochemical Physics, Russian Academy of Sciences, Kosygina st. 4, 119334 Moscow, Russian Federation
5 Department of Chemistry, M. V. Lomonosov Moscow State University, Leninskie gory 1-3, 119991 Moscow, Russian Federation

Abstract: Multi-purpose thiocyanate-containing protic ionic liquids were utilised in concert as a solvent, a Brønsted acidic catalyst, and a nucleophile source for the conversion of 4,5-dihydroxy-4,5-diarylimidazolidine-2-(thi)ones into imidazo[4,5-d]oxazolethiones and imidazo[4,5-d]thiazolones. A key advantage of this process is chemoselectivity switching by tuning the electron-donating nature of aryl substituents while carefully controlling the reaction temperature. In the case of unactivated arenes, oxazolethione was forced to rearrange into thiazolone in the new highly acidic protic ionic liquid, 1-methylpyrazolium triflate. The operationally simple experimental set-up is complemented by an eco-friendly aqueous work-up/filtration procedure providing pure crystalline products.
Cite: Ermolaev V.P. , Ratmanova N.K. , Baranov V.V. , Levina I.I. , Khrustalev V.N. , Ivanova O.A. , Kravchenko A.N. , Trushkov I.V. , Andreev I.A.
Multi-purpose thiocyanate protic ionic liquids in chemodivergent transformations of imidazolidin-2-(thi)one-based diols
Organic & Biomolecular Chemistry. 2025. V.23. P.7157-7164. DOI: 10.1039/d5ob00709g WOS Scopus OpenAlex
Identifiers:
Web of science: WOS:001527870100001
Scopus: 2-s2.0-105010601121
OpenAlex: W4411879589
Citing:
DB Citing
OpenAlex 1
Web of science 1
Scopus 1
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