1,2,4-Oxadiazole as a potential scaffold in agrochemistry: a review

Zhong, Liangkun; Wu, Changyuan; Li, Mimi; Wu, Junhui; Chen, Yang; Ju, Zhiran; Tan, Chengxia

doi:10.1039/d3ob00934c

Org. Biomol. Chem.

2023

DOI: 10.1039/d3ob00934c

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1,2,4-Oxadiazole as a potential scaffold in agrochemistry: a review

Liangkun Zhong,

Changyuan Wu,

Mimi Li

et al.

Abstract: N,O-Containing heterocycles are incorporated in various approved pesticides and pesticide candidates. The persistent challenge in modern crop protection is the continuous pursuit of novel N,O-heterocycle-containing compounds with pesticidal properties. Among...

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2024

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Cited by 5 publications

References 75 publications

(91 reference statements)

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Tetrafluoropyridinyl Thiolate as a Tool for Enabling Photoredox Alkylation of 1,2,4‐Oxadiazoles

Frumkin,

Levin,

Dilman

2024

Adv Synth Catal

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A method for the radical functionalization of 1,2,4‐oxadiazoles using alkyl halides as precursors of radicals is described. The reaction efficiency is determined by potassium tetrafluoropyridinyl thiolate additive, which plays dual role. First, the thiolate converts alkyl halides into more reactive fluorinated aryl sulfides, which undergo photoredox activation of the C‐S bond. Second, the thiolate decreases the unproductive loss of alkyl radicals by converting them back to the sulfides.

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Tetrafluoropyridinyl Thiolate as a Tool for Enabling Photoredox Alkylation of 1,2,4‐Oxadiazoles

Frumkin,

Levin,

Dilman

2024

Adv Synth Catal

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An Electrosynthesis of 1,3,4‐Oxadiazoles from N‐Acyl Hydrazones

Chen,

Thompson,

Jamieson

2024

Chemistry A European J

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The 1,3,4‐oxadiazole is a widely encountered motif in the areas of pharmaceuticals, materials, and agrochemicals. This work has established a mild, mediated electrochemical synthesis of 2,5‐disubstituted 1,3,4‐oxadiazoles from N‐acyl hydrazones. Using DABCO as the optimal redox mediator has enabled a mild oxidative cyclisation, without recourse to stoichiometric oxidants. In contrast to previous methods, this indirect electrochemical oxidation has enabled a broad range of substrates to be accessed, with yields of up to 83%, and on gram scale. The simplicity of the method has been further demonstrated by the development of a one‐pot procedure, directly transforming readily available aldehydes and hydrazides into valuable heterocycles.

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Redevelopment of limonoid as potential pesticidal resource from non-edible wastes of the citrus industry: Combinatorial synthesis and insecticidal evaluation of limonin-derived oxime ethers with scaffold diversity

Yang,

Li,

et al. 2024

Industrial Crops and Products

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1,2,4-Oxadiazole as a potential scaffold in agrochemistry: a review

Abstract: N,O-Containing heterocycles are incorporated in various approved pesticides and pesticide candidates. The persistent challenge in modern crop protection is the continuous pursuit of novel N,O-heterocycle-containing compounds with pesticidal properties. Among...

Cited by 5 publications

References 75 publications

Tetrafluoropyridinyl Thiolate as a Tool for Enabling Photoredox Alkylation of 1,2,4‐Oxadiazoles

Tetrafluoropyridinyl Thiolate as a Tool for Enabling Photoredox Alkylation of 1,2,4‐Oxadiazoles

An Electrosynthesis of 1,3,4‐Oxadiazoles from N‐Acyl Hydrazones

Redevelopment of limonoid as potential pesticidal resource from non-edible wastes of the citrus industry: Combinatorial synthesis and insecticidal evaluation of limonin-derived oxime ethers with scaffold diversity

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