Multi-purpose thiocyanate protic ionic liquids in chemodivergent transformations of imidazolidin-2-(thi)one-based diols
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-<i>d</i>]oxazolethiones and imidazo[4,5-<i>d</i>]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.
Authors
- Ирина И. Левина (ORCID: https://orcid.org/0000-0001-5791-3343)
- Victor N. Khrustalev (ORCID: https://orcid.org/0000-0001-8806-2975)
- V.N. Ermolaev (ORCID: https://orcid.org/0009-0003-1067-8464)
- Оlga А. Ivanova (ORCID: https://orcid.org/0000-0002-1651-4001)
- Владимир В. Баранов (ORCID: https://orcid.org/0000-0003-4818-7807)
- Igor V. Trushkov (ORCID: https://orcid.org/0000-0002-1614-416X)
- Ангелина Н. Кравченко (ORCID: https://orcid.org/0000-0002-6210-4775)
- Иван А. Андреев (ORCID: https://orcid.org/0000-0002-7195-0535)
- Нина К. Ратманова (ORCID: https://orcid.org/0000-0001-7602-7195)
Institutions
- Peoples' Friendship University of Russia (RU)
- D. Mendeleyev University of Chemical Technology of Russia (RU)
- Lomonosov Moscow State University (RU)
- N.D. Zelinsky Institute of Organic Chemistry (RU)
- Institute of Biochemical Physics NM Emanuel (RU)
Publication Details
- Journal
- Organic & Biomolecular Chemistry
- Published
- 2025-01-01
- DOI
- https://doi.org/10.1039/d5ob00709g
- Citations
- 1
- Primary Topic
- Chemical Synthesis and Reactions
- Type
- article
- Field-Weighted Citation Impact
- 0.94