Synthesis of Heterocyclic Chalcone Analogues Containing Chromene and 1-Hydroxyimidazole Moieties | Sciact - CRIS-system of Boreskov Institute of Catalysis

Synthesis of Heterocyclic Chalcone Analogues Containing Chromene and 1-Hydroxyimidazole Moieties Full article

Journal

Russian Journal of General Chemistry
ISSN: 1070-3632 , E-ISSN: 1608-3350

Output data

Year: 2025, Volume: 95, Number: 11, Pages: 3635-3644 Pages count : 10 DOI: 10.1134/s107036322560657x

Tags

imidazole, 5-acetylimidazole, benzopyrane, chromene, 5-formylchromene, DBU, chalcones

Authors

Basanova Elizaveta I. ¹ , Kulinich Ekaterina M. ¹ , Moskalev Ivan A. ² , Fedorov Alexey Yu. ² , Arkhipov Sergey G. ² , Yarovaya Ol'ga I. ³ , Nikitina Polina A. ¹

Affiliations

1	D.I. Mendeleyev University of Chemical Technology of Russia, Moscow, 125047 Russia
2	SRF “SKIF”, Koltsovo, 630559 Russia
3	N.N. Vorozhtsov Institute of Organic Chemistry of the Siberian Branch of the Russian Academy of Sciences, Novosibirsk, 630090 Russia

Hybrid chalcones containing 1-hydroxyimidazole and chromene moieties were synthesized from 5-acetyl-1-hydroxyimidazoles and 3-formylchromenes. Application of DBU as a catalyst led to the mixtures of the target chalсones and intermediate aldols. Further interaction of the mixtures with 40% aqueous solution of sodium hydroxide in ethanol resulted in pure chalсones, isolated as trans-isomers. According to X-ray single crystal diffraction analysis, (E)-3-{3-[2-(4-fluorophenyl)-1-hydroxy-4-methyl-1H-imidazol-5-yl]-3-oxoprop-1-en-1-yl}-6-methyl-4H-chromen-4-one exists as an N-hydroxyimidazole tautomer. Its planar structure is stabilized by the intramolecular hydrogen bond between the N-hydroxy group of the imidazole and the adjacent carbonyl group. The (E)-3-{3-[2-(4-fluorophenyl)-1-hydroxy-4-methyl-1H-imidazol-5-yl]-3-oxoprop-1-en-1-yl}-6-methyl-4H-chromen-4-one molecules in crystal were head-to-tail packed.

Basanova E.I. , Kulinich E.M. , Moskalev I.A. , Fedorov A.Y. , Arkhipov S.G. , Yarovaya O.I. , Nikitina P.A.
Synthesis of Heterocyclic Chalcone Analogues Containing Chromene and 1-Hydroxyimidazole Moieties
Russian Journal of General Chemistry. 2025. V.95. N11. P.3635-3644. DOI: 10.1134/s107036322560657x WOS Scopus OpenAlex publication_identifier_short.sciact_skif_identifier_type

Submitted:	Oct 10, 2025
Accepted:	Oct 31, 2025

Web of science:	WOS:001633597000034
Scopus:	2-s2.0-105024208117
OpenAlex:	W4417114250
publication_identifier.sciact_skif_identifier_type:	4234

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Scopus	Нет цитирований
OpenAlex	Нет цитирований