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Abstract <p>In this work, 4-[2-(3- and 4-hydroxyphenyl)ethen-1-yl]-1,2,3-thia- and selenodiazoles were obtained based on natural 4-(hydroxyphenyl)but-3-en-2-ones. Under the conditions of the phase-transfer catalyzed version of the Königs–Knorr reaction, 4-[2-(4-hydroxyphenyl)ethen-1-yl]-1,2,3-thiadiazole forms β-glycosides with low yields, while 4-[2-(3-hydroxyphenyl)ethen-1-yl]-1,2,3-thiadiazole forms labile α-glycosides. Selenodiazole analogs decompose under the reaction conditions. β-Glycosides of 4-(hydroxyphenyl)but-3-en-2-ones were prepared. Their carbethoxyhydrazones form the 1,2,3-thiadiazole when treated with thionyl chloride, and the corresponding semicarbazones are oxidized by selenium dioxide to 1,2,3-selenodiazoles.</p>

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Glycosides of 4-[2-(Hydroxyphenyl)ethen-1-yl]-1,2,3-thia- and Selenodiazoles Based on Natural 4-(Hydroxyphenyl)but-3-en-2-ones

  • 期刊论文

  • 发表日期：

    2025年9月1日

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

摘要

Abstract

In this work, 4-[2-(3- and 4-hydroxyphenyl)ethen-1-yl]-1,2,3-thia- and selenodiazoles were obtained based on natural 4-(hydroxyphenyl)but-3-en-2-ones. Under the conditions of the phase-transfer catalyzed version of the Königs–Knorr reaction, 4-[2-(4-hydroxyphenyl)ethen-1-yl]-1,2,3-thiadiazole forms β-glycosides with low yields, while 4-[2-(3-hydroxyphenyl)ethen-1-yl]-1,2,3-thiadiazole forms labile α-glycosides. Selenodiazole analogs decompose under the reaction conditions. β-Glycosides of 4-(hydroxyphenyl)but-3-en-2-ones were prepared. Their carbethoxyhydrazones form the 1,2,3-thiadiazole when treated with thionyl chloride, and the corresponding semicarbazones are oxidized by selenium dioxide to 1,2,3-selenodiazoles.