Synthesis, Characterization, and Herbicidal Activities of New 1,3,4‐Oxadiazoles, 1,3,4‐Thiadiazoles, and 1,2,4‐Triazoles Derivatives Bearing (<i>R</i>)‐5‐Chloro‐3‐fluoro‐2‐phenoxypyridine

Kalhor, Mehdi; Dadras, Akbar

doi:10.1002/jhet.950

Cited by 20 publications

(9 citation statements)

References 24 publications

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“…Clodinafop-propargyl with herbicidala ctivityw as explored in the reactionw ith 1a,g enerating 5j in ay ield of 80 %. [23] Finally,t his methodology was also applied in the derivatization of Erlotinib, whichisoften used for molecular targeted therapy, to yield 5k.A so bserved in almosta ll cases, the PcAACr eaction showede xcellent selectivity,c onversions,a nd yields,w hich represents an important finding fort he preparation of 1,4-substituted 1,2,3-triazolesw ithout the use of copper. [24] In addition, to illustrate the practicability of the reaction protocol, the PcAACr eaction could be scaled up to 1g by using 0.5 mol of the each reactant, giving as atisfactory yield of 88 % [c] [(piq) 2 Ir(acac)] DCM 6/RT,a ir,w hite LED NR 19 [d] [(piq) 2 Ir(acac)] DCM 6/RT,a ir,w hite LED NR catalystr etains its catalytic activity during continuous recycling experiments (four cycles) with considerable selectivity and efficiency.…”

Section: Resultsmentioning

confidence: 99%

Visible‐Light‐Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron‐Transfer Strategy

Liao

et al. 2020

Chemistry A European J

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Click chemistry focuseso nt he development of highly selectiver eactionsu sing simple precursors for the exquisite synthesis of molecules. Undisputedly,t he Cu I -catalyzed azide-alkyne cycloaddition (CuAAC)i so ne of the most valuable examples of click chemistry, but it suffersf rom some limitations as it requires additional reducing agents and ligands as well as cytotoxic copper. Here, we demonstrate an ovel strategy for the azide-alkyne cycloaddition reaction that involves ap hotoredox electron-transfer radical mechanism insteado ft he traditional metal-catalyzed coordination process.T his newly developed photocatalyzeda zidealkyne cycloaddition reaction can be performed under mild conditions at room temperature in the presence of air and visiblel ight ands hows good functional group tolerance, excellenta tom economy, highy ields of up to 99 %, and absolute regioselectivity,a ffordingavariety of 1,4-disubstituted 1,2,3-triazole derivatives, including bioactive molecules and pharmaceuticals. The use of ar ecyclable photocatalyst,s olar energy, andw ater as solventm akes this photocatalytic systems ustainable and environmentally friendly.M oreover, the azide-alkyne cycloadditionr eaction could be photocatalyzed in the presenceo fametal-free catalyst with excellent regioselectivity,w hich represents an important development for click chemistry and should find versatile applicationsi n organic synthesis, chemical biology,and materials science.[a] Dr.Scheme1.Structures of 1,4-disubstituted 1,2,3-triazoles and strategies for their synthesis. (a) Bioactive molecules and pharmaceuticals based on the 1,4-disub-stituted1 ,2,3-triazole core. (b) The reported methodsf or the synthesis of 1,4-disubstituted 1,2,3-triazoles and the mechanism for the traditional metal-catalyzed AAC reaction. (c)Our designed strategy for the AAC reaction through photoredox electron-transfer cyclization and its features andadvantages, as well as the proposed mechanism.( Figure 1a). The recyclability of the photocatalystwas also evaluated and the resultsd emonstrate that the photocatalyst is air-and moisture-tolerant and can be readily recovered after use and reused severalt imes. Figure 1b shows that the photo-Scheme2.Scope of the PcAAC reaction.Standardreagents and conditions: Azide (0.2 mmol), alkyne (0.2 mmol), photocatalyst (5 mol %), DCM (2.0 mL), RT, air,6 -12 h, 26 Ww hite LED irradiation.

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Section: Resultsmentioning

confidence: 99%

Visible‐Light‐Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron‐Transfer Strategy

Liao

et al. 2020

Chemistry A European J

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“…Lin et al [ 29 , 30 ] integrated a benzofuran unit into the scaffold of aryloxy phenoxycarboxylic acid amide to yield Compound 9 . Compound 9 exhibited 100% control efficiency at the concentration of 2250 g/hm 2 at both pre- and post-emergence applications.…”

Section: Herbicides Containing Phenoxypyridine Scaffoldmentioning

confidence: 99%

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

Liu

Yong

et al. 2022

Molecules

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Phenoxypyridine, the bioisostere of diaryl ethers, has been widely introduced into bioactive molecules as an active scaffold, which has different properties from diaryl ethers. In this paper, the bioactivities, structure-activity relationships, and mechanism of compounds containing phenoxypyridine were summarized, which may help to explore the lead compounds and discover novel pesticides with potential bioactivities.

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“…The authors extrapolated this methodology, using it to synthesize a derivative of vilazodone (135, Scheme 40C), a known antidepressant drug commercialized under the name viibryd which also bears potential activity against Parkinson's disease [203]. In previous studies it has been observed that 2-phenoxypyridines belong to a class of compounds that presents potent herbicidal properties (136, 137, Scheme 41A) [204]. Chelated cobalt(II) catalysts, such as [Co(acac) 2 ], can also be used in C-H activation methods to modify 2-phenoxypyridines, from which other biological activities can be discovered.…”

Section: Cobalt-catalyzed C-h Activationmentioning

confidence: 99%

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

Carvalho¹,

Miranda²,

Nunes³

et al. 2021

Beilstein J. Org. Chem.

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Several valuable biologically active molecules can be obtained through C–H activation processes. However, the use of expensive and not readily accessible catalysts complicates the process of pharmacological application of these compounds. A plausible way to overcome this issue is developing and using cheaper, more accessible, and equally effective catalysts. First-row transition (3d) metals have shown to be important catalysts in this matter. This review summarizes the use of 3d metal catalysts in C–H activation processes to obtain potentially (or proved) biologically active compounds.

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Synthesis, Characterization, and Herbicidal Activities of New 1,3,4‐Oxadiazoles, 1,3,4‐Thiadiazoles, and 1,2,4‐Triazoles Derivatives Bearing (R)‐5‐Chloro‐3‐fluoro‐2‐phenoxypyridine

Cited by 20 publications

References 24 publications

Visible‐Light‐Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron‐Transfer Strategy

Visible‐Light‐Mediated Click Chemistry for Highly Regioselective Azide–Alkyne Cycloaddition by a Photoredox Electron‐Transfer Strategy

Advancement of Phenoxypyridine as an Active Scaffold for Pesticides

On the application of 3d metals for C–H activation toward bioactive compounds: The key step for the synthesis of silver bullets

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