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Abstract <p>2-Aryl- and 2-aryl-5-alkyl-1,3,4-oxadiazoles were synthesized by the interaction of benzoic acid hydrazides with orthoesters of carboxylic acids, and their antiradical action was studied in the reaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH<sup>•</sup>). In the reaction with DPPH<sup>•</sup>, phenoloxadiazoles showed higher antiradical activity compared to the corresponding monohydroxybenzoic acids due to intramolecular synergism, which is a result of the combined action of the phenol and oxadiazole fragments within one molecule, leading to resonance stabilization of the resulting phenoxyl radical. For 1,3,4-oxadiazoles, which do not contain a phenolic fragment in their composition and exhibit lower antiradical activity compared to phenoloxadiazoles, a mechanism of their antioxidant action has been proposed, which is associated with the formation of a radical adduct.</p>

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Synthesis and Antioxidant Properties of 1,3,4-Oxadiazole Derivatives of Benzoic and Monohydroxybenzoic Acids

  • 期刊论文

  • 发表日期：

    2025年6月1日

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  • I. E. Mikhailov,
  • N. I. Belaya,
  • A. V. Belyi,
  • Yu. M. Artyushkina,
  • G. A. Dushenko,
  • V. I. Minkin

摘要

Abstract

2-Aryl- and 2-aryl-5-alkyl-1,3,4-oxadiazoles were synthesized by the interaction of benzoic acid hydrazides with orthoesters of carboxylic acids, and their antiradical action was studied in the reaction with 2,2-diphenyl-1-picrylhydrazyl (DPPH•). In the reaction with DPPH•, phenoloxadiazoles showed higher antiradical activity compared to the corresponding monohydroxybenzoic acids due to intramolecular synergism, which is a result of the combined action of the phenol and oxadiazole fragments within one molecule, leading to resonance stabilization of the resulting phenoxyl radical. For 1,3,4-oxadiazoles, which do not contain a phenolic fragment in their composition and exhibit lower antiradical activity compared to phenoloxadiazoles, a mechanism of their antioxidant action has been proposed, which is associated with the formation of a radical adduct.