Triple‐Purpose Thiocyanate‐Containing Protic Ionic Liquids: Chemodivergent Transformations of Dihydroimidazolones into Imidazo[4,5‐d]oxazolethiones and Imidazo[4,5‐d]thiazolones

Triple‐Purpose Thiocyanate‐Containing Protic Ionic Liquids: Chemodivergent Transformations of Dihydroimidazolones into Imidazo[4,5‐d]oxazolethiones and Imidazo[4,5‐d]thiazolones Full article

Journal

Asian Journal of Organic Chemistry
ISSN: 2193-5815 , E-ISSN: 2193-5807

Output data

Year: 2025, Volume: 14, Number: 2, Article number : e202400338, Pages count : DOI: 10.1002/ajoc.202400338

Authors

Ratmanova Nina ¹ , Ermolaev Valery ² , Baranov Vladimir V ³ , Levina Irina ⁴ , Minyaev Mikhail ³ , Ivanova Olga ⁵ , Kravchenko Angelina ³ , Trushkov Igor ³ , Andreev Ivan ¹

Affiliations

1	Dmitry Rogachev National Medical Research Center of Pediatric Hematology Oncology and Immunology, Laboratory of Chemical Synthesis, Moscow, RUSSIAN FEDERATION
2	D. I. Mendeleev Russian University of Chemical Technology, Higher Chemical College of the Russian Academy of Sciences, Moscow, RUSSIAN FEDERATION
3	Zelinsky Institute of Organic Chemistry RAS, Moscow, RUSSIAN FEDERATION
4	FEBSI Institute of Biochemical Physics named after N M Emanuel of the Russian Academy of Sciences, NMR Center, Moscow, RUSSIAN FEDERATION
5	Lomonosov Moscow State University, Department of Chemistry, Moscow, RUSSIAN FEDERATION

Triple-purpose protic ionic liquids were employed as a solvent, a Brønsted acid catalyst, and a source of the nucleophile (thiocyanate-ion) for the chemodivergent transformation of dihydroimidazolones into 2-thioxohexahydro-5H-imidazo[4,5-d]oxazol-5-ones and tetrahydro-2H-imidazo[4,5-d]thiazole-2,5(3H)-diones. An important feature of this process is the switching of its chemoselectivity by simple variation of the reaction temperature, other conditions being the same; this allowed both types of products to be obtained selectively. Straightforward aqueous work-up of reaction mixture provided crystalline bicyclic products in pure form in an environmentally friendly manner.

Ratmanova N. , Ermolaev V. , Baranov V.V. , Levina I. , Minyaev M. , Ivanova O. , Kravchenko A. , Trushkov I. , Andreev I.
Triple‐Purpose Thiocyanate‐Containing Protic Ionic Liquids: Chemodivergent Transformations of Dihydroimidazolones into Imidazo[4,5‐d]oxazolethiones and Imidazo[4,5‐d]thiazolones
Asian Journal of Organic Chemistry. 2025. V.14. N2. e202400338 . DOI: 10.1002/ajoc.202400338 WOS OpenAlex

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