Trifluoroacetimidoyl Chlorides Research Articles

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

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.

Carbonylative synthesis of 2-(trifluoromethyl)quinazolin-4(3H)-ones from trifluoroacetimidoyl chlorides and amines based on an activated carbon fiber supported palladium catalyst

Activated carbon fibers, known for their unique physical and chemical properties, are increasingly utilized in diverse industries, including textiles and fabrics, and can serve as ideal supports of heterogeneous palladium catalysts.

Construction of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides and derivatives.

Recent advances in the direct synthesis of trifluoromethyl-containing heterocycles from trifluoroacetimidoyl chlorides (TFAICs) and derivatives, including trifluoroacetimidohydrazides (TFAIHs) and CF3-imidoyl sulfoxonium ylides (TFISYs), are systematically summarized and discussed. The cascade annulation reactions of trifluoromethyl-containing synthons with suitable coupling partners have emerged as a powerful and promising tool for the construction of a variety of trifluoromethyl-substituted heterocycles. Compared with other trifluoromethyl-containing building blocks, TFAICs and derivatives have notable merits of easy availability and handling, relative stability and safety, and high reactivity.

Palladium-catalyzed four-component cascade carbonylative cyclization to access carbonyl-bridged bisheterocycles

We developed a palladium-catalyzed four-component carbonylative cyclization of alkenyl-tethered aryl iodides, trifluoroacetimidoyl chlorides and propargyl amines for the construction of carbonyl-bridged bisheterocycles.

Metal-free synthesis of 3-trifluoromethyl-1,2,4-triazoles via multi-component reaction of trifluoroacetimidoyl chlorides, hydrazine hydrate and benzene-1,3,5-triyl triformate.

A convenient approach for the construction of pharmaceutically valuable 3-trifluoromethyl-1,2,4-triazoles has been developed, which employs the readily available trifluoroacetimidoyl chlorides, hydrazine hydrate and benzene-1,3,5-triyl triformate (TFBen) as starting materials. The multi-component reaction features broad substrate scope, high efficiency, and scalability, providing a facile and straightforward route to the biologically important 3-trifluoromethyl-1,2,4-triazole scaffolds in moderate to good yields. Considering its broad-spectrum pharmaceutical activity, the method offers the opportunity for the further study towards the toxicity risk assessment and structure-activity relationship of the pharmaceuticals containing trifluoromethyl-1,2,4-triazole cores.

Survey reactions of gabapentin with trifluoroacetimidoyl chlorides or trialkyl phosphites

Survey reactions of gabapentin with trifluoroacetimidoyl chlorides or trialkyl phosphites

Palladium-catalyzed norbornene-mediated dehydrogenative annulation of 3-iodochromones with trifluoroacetimidoyl chlorides for the construction of trifluoromethyl-substituted chromeno[2,3-c]quinolin-12-ones

A straightforward approach for the synthesis of various trifluoromethyl-substituted chromeno[2,3-c]quinolin-12-ones has been developed, which employs a palladium-catalyzed norbornene-mediated dehydrogenative annulation of readily available 3-iodochromones with trifluoroacetimidoyl chlorides. The domino strategy involving Pd/NBE cooperative catalysis provides a powerful tool for preparing chromone- and trifluoromethyl-containing fused-heterocyclic compounds.

Controllable access to trifluoromethyl-containing indoles and indolines: palladium-catalyzed regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides.

The synthesis of diverse products from the same starting materials is always attractive in organic chemistry. Here, a palladium-catalyzed substrate-controlled regioselective functionalization of unactivated alkenes with trifluoroacetimidoyl chlorides has been developed, which provides a direct but controllable access to a variety of structurally diverse trifluoromethyl-containing indoles and indolines. In more detail, with respect to γ,δ-alkenes, 1,1-geminal difunctionalization of unactivated alkenes with trifluoroacetimidoyl chloride enables the [4 + 1] annulation to produce indoles; as for β,γ-alkenes, a [3 + 2] heteroannulation with the hydrolysis product of trifluoroacetimidoyl chloride through 1,2-vicinal difunctionalization of alkenes occurs to deliver indoline products. The structure of alkene substrates differentiates the regioselectivity of the reaction.

Synthesis of 1-Amino-2,2,2-trifluoroalkylphosphonates from Alkene-Tethered Trifluoroacetimidoyl Chlorides.

The reaction of alkene-tethered trifluoroacetimidoyl chlorides with trialkyl phosphites furnishes 1-amino-2,2,2-trifluoroalkylphosphonates. The products were generated in moderate to good yields, and the scalability of this process was showcased. Partial hydrolysis of the phosphonate moiety was achieved. The cyclization is proposed to occur via formation of an imidoyl phosphonate intermediate that becomes susceptible to nucleophilic attack at nitrogen through the strong electron-withdrawing groups at the imidoyl carbon.

Efficient synthesis of 2-trifluoromethyl-benzimidazoles via cascade annulation of trifluoroacetimidoyl chlorides and amines based on a heterogeneous copper doped g-C3N4 catalyst

• A heterogeneous copper doped g-C 3 N 4 catalyst has been prepared. • An efficient approach for synthesis of 2-trifluoromethyl-benzimidazoles has been developed. • higher catalytic reactivity of the Cu/g-C 3 N 4 catalyst compared with homogeneous copper catalyst was observed. An efficient approach for the synthesis of 2-trifluoromethyl-benzimidazoles via cascade annulation of trifluoroacetimidoyl chlorides and amines using a heterogeneous copper doped g-C 3 N 4 catalyst has been developed. Compared with the previously reported homogeneous catalytic system, the reaction exhibits higher efficiency and the copper doped g-C 3 N 4 catalyst can be readily recycled for three times with slightly decreased catalytic reactivity. An efficient approach for synthesis of 2-trifluoromethyl-benzimidazoles through cascade annulation of trifluoroacetimidoyl chlorides and amines base on a heterogeneous Cu/g-C 3 N 4 catalyst has been reported. The protocol enables the formation of various 2-trifluoromethyl-benzimidazoles in up to 99% yield and the Cu/g-C 3 N 4 catalyst can be recycled for three times.

Planar chiral 2-(trifluoromethyl)quinoline-fused ferrocenes via palladium(0)-catalyzed C-H functionalization of trifluoroacetimidoyl chlorides

Catalytic enantioselective synthesis of planar chiral 2-(trifluoromethyl)quinoline-fused ferrocenes has been achieved through Pd(0)-catalyzed C-H functionalization with trifluoroacetimidoyl chlorides as electrophilics. With commercially available ligand and palladium precursor, the reaction proceeds smoothly generating 2-perfluoroalkylated quinoline-fused ferrocenes in high yields and enantioselectivities.

Palladium-catalyzed synthesis of novel trifluoromethylated quinazolinone, N-arylquinazoline and N-benzylquinazoline derivatives

A simple and palladium-catalyzed procedure for synthesis of a novel series of potentially biologically active trifluoromethyl-substituted quinazolinones and N-arylquinazoline derivatives via condensation-cyclization reaction of 2-aminobenzamide, 2-amino-N′-arylbenzimidamides and 2-amino-N′-benzylbenzimidamides with trifluoroacetimidoyl chlorides has been developed. noteworthy, this investigation showed the possible of transition-metal-catalyzed activation of trifluoroacetimidoyl chlorides as a carbon trifluoromethylated source for the synthesis of quinazolines and quinazolinone derivatives in good to excellent yields.

Silver-Mediated [3 + 2] Cycloaddition of Azomethine Ylides with Trifluoroacetimidoyl Chlorides for the Synthesis of 5-(Trifluoromethyl)imidazoles.

A silver-mediated [3 + 2] cycloaddition of azomethine ylides with trifluoroacetimidoyl chlorides for the rapid assembly of 5-(trifluoromethyl)imidazoles has been developed. Notable features of the reaction include readily accessible reagents, a broad substrate scope, and high efficiency. The protocol can be successfully applied to construct the analogue of the specific allosteric modulator of GABAA receptors. The silver species could be recycled by a simple operation.

Palladium‐Catalyzed Carbonylative Synthesis of 2‐(Trifluoromethyl)quinazolin‐4(3H)‐ones from Trifluoroacetimidoyl Chlorides and Nitro Compounds

AbstractA procedure on palladium‐catalyzed carbonylative reaction of trifluoroacetimidoyl chlorides and nitro compounds for the construction of pharmaceutically valuable 2‐(trifluoromethyl)quinazolin‐4(3H)‐ones has been achieved. In this transformation, Mo(CO)6 has been used both as a convenient CO source and a reducing reagent. This newly developed protocol is compatible with various nitro compounds and can be readily scaled up to 1 mmol scale.magnified image

Synthesis of 5-trifluoromethyl-1,2,3-triazoles via base-mediated cascade annulation of diazo compounds with trifluoroacetimidoyl chlorides

A metal-, azide- and CF3-reagent free approach for the synthesis of 5-trifluoromethyl-1,2,3-triazoles via base-mediated cascade annulation of diazo compounds with trifluoroacetimidoyl chlorides has been developed.

The cascade coupling/iodoaminocyclization reaction of trifluoroacetimidoyl chlorides and allylamines: metal-free access to 2-trifluoromethyl-imidazolines.

A metal-free cascade coupling/iodoaminocyclization reaction for the rapid assembly of 2-trifluoromethyl-imidazolines has been disclosed. The transformation applies readily accessible trifluoroacetimidoyl chlorides, allylamines and N-iodosuccinimides as the starting substrates, achieving an efficient and straightforward pathway to construct diverse imidazoline derivatives. Excellent efficiency of the reaction is observed (higher than 90% isolated yield for half of the examples), and the obtained imidazoline products bearing a pendent iodomethyl group could be easily transformed into other synthetically valuable compounds.

Copper-mediated [3 + 2] cycloaddition of trifluoroacetimidoyl chlorides and N-isocyanoiminotriphenylphosphorane for the synthesis of 3-trifluoromethyl-1,2,4-triazoles

Herein, a facile and straightforward route to synthesize 3-trifluoromethyl-1,2,4-triazoles via copper-mediated [3 + 2] cycloaddition of trifluoroacetimidoyl chlorides and N-isocyanoiminotriphenylphosphorane (NIITP) has been described.

I2/KI-Catalyzed synthesis of 5-trifluoromethylated 1,2,4,6-tetrazepine-3-thiones by annulation of trifluoroacetimidoyl chlorides and thiosemicarbazones

An efficient and simple protocol for the synthesis of trifluoromethylated 1,2,4,6-tetrazepines by intramolecular cross-coupling of C(sp2)–H and N–H bonds using I2/KI catalyst under aerobic oxidative has been demonstrated. This research exhibited a nucleophilic substitution reaction and then oxidative cyclization between trifluoroacetimidoyl chlorides and thiosemicarbazones.

A Convenient FeCl3‐Mediated Synthesis of 5‐Trifluoromethyl‐1,2,4‐triazoles from Trifluoroacetimidoyl Chlorides and Hydrazides

AbstractA low cost FeCl3‐mediated cascade annulation of trifluoroacetimidoyl chlorides and hydrazides for the efficient synthesis of 5‐trifluoromethyl‐1,2,4‐triazoles has been developed. The transformation proceeds through a cascade base‐promoted intermolecular C−N bond formation and FeCl3‐mediated intramolecular dehydration sequence under mild conditions. The protocol exhibits many notable features and can be readily scaled up to gram scale.magnified image

Palladium‐Catalyzed Cascade Carbonylative Cyclization Reaction of Trifluoroacetimidoyl Chlorides and 2‐Iodoanilines: Toward 2‐(Trifluoromethyl)quinazolin‐4(3H)‐ones Synthesis

AbstractA palladium‐catalyzed cascade carbonylative/cyclization reaction for the synthesis of 2‐(trifluoromethyl)quinazolin‐4(3H)‐ones has been achieved. The transformation utilizes readily available 2‐iodoanilines and trifluoroacetimidoyl chlorides as the starting reagents, enabling a simple and convenient access to pharmaceutically significant quinazolin‐4(3H)‐one derivatives.