A simple synthesis of trifluoromethylated pyridinium azomethine ylides by three-component reaction between pyridines, phenacyl bromides, and N-aryltrifluoroacetimidoyl chlorides

Talebizadeh, Mahdiyeh; Anary‐Abbasinejad, Mohammad; Darekordi, Ali

doi:10.1007/s10593-019-02447-z

Cited by 3 publications

(1 citation statement)

References 22 publications

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“…6 It has been demonstrated that fluorine gives unique effects to the organic molecules that contain it and improves their physicochemical and biological properties. Among fluorinated substituents, the trifluoromethyl group (CF3) has received attention in the medicinal, agricultural, and material sciences 7 due to its influence on the physical, chemical, and physiological, stability and lipophilicity properties of the molecules incorporating this group. 8 Furthermore, recent research effort on trifluoroacetimidoyl chlorides has led to synthesis of trifluoromethylated heterocycles.…”

Section: Introductionmentioning

confidence: 99%

Survey reactions of gabapentin with trifluoroacetimidoyl chlorides or trialkyl phosphites

darehkordi¹,

Rezaei²,

Nejad³

et al. 2022

Arkivoc

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Synthesis of a new class of 2-[1-({[2,2,2-trifluoro-1-(arylamino)ethylidene]amino}methyl)cyclohexyl]acetic acids and 2,2,2-trifluoro-N-({1-[2-oxo-2-(arylamino)ethyl]cyclohexyl}methyl)acetamides are described by one-pot reaction of gabapentin and trifluoroacetimidoyl chlorides in the presence and absence of titanium dioxide nanoparticles (TiO2-NPs) as a catalyst and sodium hydride as a base under an N2 atmosphere. Subsequently, a series of potentially biologically active of 2-[1({[(dialkoxyphosphoryl)(phenyl)methyl]amino}methyl)cyclohexyl] acetic acid derivatives were synthesized via reaction of gabapentin, benzaldehyde imino derivatives and trialkyl phosphites in the presence of I2/CH3COOH as catalyst. The structures of products are supported by FT-IR, 1 H-NMR, 13 C-NMR, 19 F-NMR spectral and X-Ray crystallography data.

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Section: Introductionmentioning

confidence: 99%

Survey reactions of gabapentin with trifluoroacetimidoyl chlorides or trialkyl phosphites

darehkordi¹,

Rezaei²,

Nejad³

et al. 2022

Arkivoc

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Application of phenacyl bromide analogs as a versatile organic intermediate for the synthesis of heterocyclic compounds via multicomponent reactions

Javahershenas

2022

Mol Divers

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A Novel Bis-Trifluoromethylated Compound Demonstrates High Efficacy as a Nematicide Against Root-Knot Nematodes on Pistachio, Supported by Docking Studies

Khatamidoost,

Darehkordi,

Saremi

et al. 2024

Phytopathology®

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Three novel trifluoromethylated compounds were designed and synthesized by reacting trifluoroacetimidoyl chloride derivatives with acetamidine hydrochloride or thiourea in the presence of potassium carbonate or sodium hydrogen carbonate as a base. In vitro and in vivo assays demonstrated the efficacy of the tested compounds in controlling root-knot nematode disease on pistachio rootstocks caused by Meloidogyne incognita. Bis-trifluoromethylated derivatives, namely N, N′′-thiocarbonylbis( N′-(3,4-dimethylphenyl)-2,2,2-trifluoroacetimidamide) (compound A1), showed high efficacy as novel and promising nematicides, achieving up to 78.28% control at a concentration of 0.042 mg/liter. This effect is attributed to four methyl and two trifluoromethyl groups. In the pre-inoculation application of compound A1, all three concentrations (0.033, 0.037, and 0.042 mg/liter, and Velum) exhibited a higher level of control, with 83.79, 87.46, and 80.73% control, respectively. In the microplot trials, compound A1 effectively reduced population levels of M. incognita and enhanced plant growth at a concentration of 0.037 mg/liter. This suggests that compound A1 has the potential to inhibit hedgehog protein and could be utilized to prevent the progression of root-knot disease. Furthermore, the molecular docking results revealed that compounds A1 and A3 interact with specific amino acid residues (Gln60, Asp530, Glu70, Arg520, and Thr510) located in the active site of hedgehog protein. Based on the experimental findings of this study, compound A1 shows promise as a lead compound for future investigations.

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A simple synthesis of trifluoromethylated pyridinium azomethine ylides by three-component reaction between pyridines, phenacyl bromides, and N-aryltrifluoroacetimidoyl chlorides

Cited by 3 publications

References 22 publications

Survey reactions of gabapentin with trifluoroacetimidoyl chlorides or trialkyl phosphites

Survey reactions of gabapentin with trifluoroacetimidoyl chlorides or trialkyl phosphites

Application of phenacyl bromide analogs as a versatile organic intermediate for the synthesis of heterocyclic compounds via multicomponent reactions

A Novel Bis-Trifluoromethylated Compound Demonstrates High Efficacy as a Nematicide Against Root-Knot Nematodes on Pistachio, Supported by Docking Studies

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