A Concise Synthesis of Azoxystrobin using a Suzuki Cross-Coupling Reaction

Liu, Yong-Gan; Luo, Yan; Lu, Yao

doi:10.3184/174751915x14418863197125

Cited by 2 publications

(2 citation statements)

References 15 publications

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“…Target compounds 6 and 7 were synthesized based on methods reported in the literature [21][22][23]. The synthetic routes of target compounds 6 and 7 are described in Scheme 2; Scheme 3.…”

Section: Synthetic Proceduresmentioning

confidence: 99%

Design, Synthesis, Crystal Structure, and Fungicidal Activity of Two Fenclorim Derivatives

Xiong

Feng-Pei

2020

Crystals

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Two fenclorim derivatives (compounds 6 and 7) were synthesized by linking active sub-structures using fenclorim as the lead compound. The chemical structures of the two compounds were confirmed by NMR spectroscopy, high resolution mass spectrometry, and X-ray diffraction analysis. Their fungicidal activity against six plant fungal strains was tested. Compounds 6 and 7 both crystallized in the monoclinic system, with a P21/c space group (a = 8.4842(6) Å, b = 24.457(2) Å, c = 8.9940(6) Å, V = 1855.0(2) Å3, Z = 4) and Cc space group (a = 10.2347(7) Å, b = 18.3224(10) Å, c = 7.2447(4) Å, V = 1357.50(14) Å3, Z = 4), respectively. The crystal structure of compound 6 was stabilized by C–H···N and C–H···O hydrogen bonding interactions and N–H···N hydrogen bonds linked the neighboring molecules of compound 7 to form a three-dimensional framework. Compound 6 displayed the most excellent activity, which is much better than that of pyrimethanil against Botrytis cinerea in vivo. Additionally, compound 6 exhibited greater in vitro activity against Pseudoperonospora cubensis compared to that of pyrimethanil. Moreover, compound 7 exhibited strong fungicidal activity against Erysiphe cichoracearum at 50 mg/L in vitro, while pyrimethanil did not. Compounds 6 and 7 could be used as new pyrimidine fungicides in the future.

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“…Target compounds 6 and 7 were synthesized based on methods reported in the literature [21][22][23]. The synthetic routes of target compounds 6 and 7 are described in Scheme 2; Scheme 3.…”

Section: Synthetic Proceduresmentioning

confidence: 99%

Design, Synthesis, Crystal Structure, and Fungicidal Activity of Two Fenclorim Derivatives

Xiong

Feng-Pei

2020

Crystals

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“…Multiple synthetic routes of Azoxystrobin have been disclosed by Zeneca (Syngenta′s predecessor) and other sources. , Among these reported methods, the prevalent approach involves the use of the industrial raw material 2-hydroxyphenylacetic acid to synthesize the intermediate methyl-2-(2-hydroxyphenyl)-3,3-dimethoxypropanoate ( 2 ), as outlined in Scheme . The crucial step in Azoxystrobin synthesis involves the cross-coupling of (E)-methyl-2-[2-(6-chloropyrimidin-4-yloxy) phenyl]-3-methoxyacrylate ( 3 ) and 2-cyanophenol ( 4 ).…”

Section: Introductionmentioning

confidence: 99%

Development of a Trimethylamine-Catalyzed Novel Synthesis of Azoxystrobin

Yang¹,

Xue²,

Yu³

et al. 2023

Org. Process Res. Dev.

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We report the development of a novel method for the synthesis of Azoxystrobin, which employs trimethylamine as a catalyst. This appealing catalytic system offers several advantages, including low cost, excellent reactivity, easy recovery, and the ability to be used repeatedly with minimal environmental impact. Mechanistic studies and density functional theory (DFT) calculations suggest that the involvement of a highly active quaternary ammonium salt intermediate is likely responsible for the efficient catalysis. This can be attributed to the low steric hindrance, flexible bare nature of the lone pair of electrons on the nitrogen atom, and low activation energy barrier of trimethylamine. These findings hold great promise for the mass production of Azoxystrobin.

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A Concise Synthesis of Azoxystrobin using a Suzuki Cross-Coupling Reaction

Abstract: A simple, efficient and eco-friendly process for the synthesis in good yield of azoxystrobin from 2-bromophenol has been developed using phenolic hydroxyl protection, Grignard reaction, Suzuki cross-coupling, hydrogenation and a nucleophilic reaction on a 2-chloropyrimidine.

Cited by 2 publications

References 15 publications

Design, Synthesis, Crystal Structure, and Fungicidal Activity of Two Fenclorim Derivatives

Design, Synthesis, Crystal Structure, and Fungicidal Activity of Two Fenclorim Derivatives

Development of a Trimethylamine-Catalyzed Novel Synthesis of Azoxystrobin

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