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Abstract <p>Phosphorylated derivatives of furanсarbaldehydes and furanylacetic aldehydes containing an ester and <i>tert</i>-butyl groups in the ring were synthesized. Their behavior in the Wittig reaction with resonance-stabilized acylmethylenetriphenylphosphoranes was studied. The resulting furanylalkenes are heterocyclic analogues of <i>trans</i>-chalcones. The compounds obtained by reaction with acetylmethylenetriphenylphosphorane were used as starting substrates for the synthesis of (<i>E</i>)-[2-(1,2,3-selenodiazol-4-yl)ethen-1-yl]furans, heterocyclic analogues of <i>trans</i>-stilbenes. Furanylacetic aldehydes form two isomers in the Wittig reaction, differing in the position of the double bond in the propene fragment. All obtained unsaturated ketones react with hydrazine to form 3,5-disubstituted 4,5-dihydro-1<i>H</i>-pyrazoles.</p>

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Phosphonomethylated 5-tert-Butylfuranyl Aldoesters: Preparation and Use in the Synthesis of Hybrid Heterocyclic Systems

  • 期刊论文

  • 发表日期：

    2025年2月1日

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  • L. M. Pevzner,
  • M. L. Petrov,
  • A. V. Stepakov

摘要

Abstract

Phosphorylated derivatives of furanсarbaldehydes and furanylacetic aldehydes containing an ester and tert-butyl groups in the ring were synthesized. Their behavior in the Wittig reaction with resonance-stabilized acylmethylenetriphenylphosphoranes was studied. The resulting furanylalkenes are heterocyclic analogues of trans-chalcones. The compounds obtained by reaction with acetylmethylenetriphenylphosphorane were used as starting substrates for the synthesis of (E)-[2-(1,2,3-selenodiazol-4-yl)ethen-1-yl]furans, heterocyclic analogues of trans-stilbenes. Furanylacetic aldehydes form two isomers in the Wittig reaction, differing in the position of the double bond in the propene fragment. All obtained unsaturated ketones react with hydrazine to form 3,5-disubstituted 4,5-dihydro-1H-pyrazoles.