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Abstract <p>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 <i>trans</i>-isomers. According to X-ray single crystal diffraction analysis, (<i>E</i>)-3-{3-[2-(4-fluorophenyl)-1-hydroxy-4-methyl-1<i>H</i>-imidazol-5-yl]-3-oxoprop-1-en-1-yl}-6-methyl-4<i>H</i>-chromen-4-one exists as an <i>N</i>-hydroxyimidazole tautomer. Its planar structure is stabilized by the intramolecular hydrogen bond between the <i>N</i>-hydroxy group of the imidazole and the adjacent carbonyl group. The (<i>E</i>)-3-{3-[2-(4-fluorophenyl)-1-hydroxy-4-methyl-1<i>H</i>-imidazol-5-yl]-3-oxoprop-1-en-1-yl}-6-methyl-4<i>H</i>-chromen-4-one molecules in crystal were head-to-tail packed.</p>

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

  • 期刊论文

  • 发表日期：

    2025年11月1日

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  • Elizaveta I. Basanova,
  • Ekaterina M. Kulinich,
  • Ivan A. Moskalev,
  • Alexey Yu. Fedorov,
  • Sergey G. Arkhipov,
  • Ol’ga I. Yarovaya,
  • Polina A. Nikitina

摘要

Abstract

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.