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

Yang, Hongchao; Xu, Tianhui; Lu, Shu-Ning; Chen, Zhengkai; Wu, Xiao‐Feng

doi:10.1039/d1qo00445j

Cited by 27 publications

(22 citation statements)

References 49 publications

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“…18 Fluorine can lead to improve the electronegativity, bioavailability, lipophilicity, and metabolic stability of fluorinated molecules. 19 Among fluorinated heterocyclic compounds, trifluoromethyl-substituted 1,2,4-triazoles as the important component of many drugs and inhibitors have attracted enormous notice from the chemical community. 20 Also fungicidal activities of 1,2,4-triazoles mostly increase by introducing fluorine atoms into these compounds.…”

Section: Paper Synthesismentioning

confidence: 99%

“…All NMR spectra were recorded on a Varian model UNITYInova 500 MHz ( 1 H: 500 13 C: 125, 19 F: 470.3 MHz) NMR spectrometer. Chemical shifts for 1 H and 13 C NMR are reported in parts per million from TMS as an internal standard and for 19 F NMR in parts per million from CFCl 3 as an internal standard, in DMSO-d 6 as the solvent; the coupling constants J are given in Hz and spectra were recorded in parts per million (ppm). Elemental analyses (CHN) were performed with a EUROVECTOR EuroEA3000 CHNSO analyzer.…”

Section: Paper Synthesismentioning

confidence: 99%

“…For these reactions FeCl 3 was used as a Lewis acid (Method b). The structures of all the products were identified by IR, 1 H NMR, 13 C NMR, and 19 F NMR spectra.…”

Section: Synthesismentioning

confidence: 99%

“…H NMR (500 MHz, DMSO-d 6 ):  = 7.50 (s, 1 H, HAr), 7.45 (d, J = 8.1 Hz, 1 H, HAr), 7.35 (d, J = 8.1 Hz, 1 H, HAr), 2.30 (s, 3 H, CH 3 ), 2.25 (s, 3 H, CH 3 ) 13. C NMR (125 MHz, DMSO-d 6 ):  = 147.07 (q, 2 J C,F = 38.6 Hz), 140.89, 138.39, 130.69, 128.57, 128.19, 125.14, 117.85 (q, 1 J C,F = 269.9 Hz),19.64 (CH 3 ),19.56 (CH 3 ).…”

mentioning

confidence: 99%

“…Zeinali, A. DarehkordiPaper Synthesis1 H NMR (500 MHz, CDCl 3 ):  = 7.27 (d, J = 9.0 Hz, 2 H, HAr), 7.04 (d, J = 9.0 Hz, 2 H, HAr), 3.90 (s, 3 H, OCH 3 ) 13. C NMR (125 MHz, CDCl 3 ):  = 161.80, 147.65 (q, 2 J C,F = 38.8 Hz), 128.19, 122.61, 117.42 (q, 1 J C,F = 270.6 Hz), 114.91, 55.65 (OCH 3 ) 19. F NMR (470.33 MHz, CDCl 3 ):  = -61.55.…”

mentioning

confidence: 99%

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Trifluoromethylated Amidrazone Derivatives as Key Compounds for the Synthesis of 4-Aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles

Zeinali¹,

Darehkordi²

2022

Synthesis

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A novel, efficient, and solvent-free approach for the synthesis of aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles has been disclosed via the nucleophilic intramolecular cyclization reaction of trifluoromethylated amidrazone and 2,2,2-trifluoroacetic anhydride. Trifluoromethylated amidrazones intermediates which are used in this project have been synthesized from the reaction of N-aryl-2,2,2-trifuoroacetimidoyl chloride derivatives and hydrazine hydrate at ambient temperature in excellent yields.

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Section: Paper Synthesismentioning

confidence: 99%

Section: Paper Synthesismentioning

confidence: 99%

“…For these reactions FeCl 3 was used as a Lewis acid (Method b). The structures of all the products were identified by IR, 1 H NMR, 13 C NMR, and 19 F NMR spectra.…”

Section: Synthesismentioning

confidence: 99%

mentioning

confidence: 99%

mentioning

confidence: 99%

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Trifluoromethylated Amidrazone Derivatives as Key Compounds for the Synthesis of 4-Aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles

Zeinali¹,

Darehkordi²

2022

Synthesis

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Copper‐Catalyzed Decarbonylative Cyclization of Isatins and Trifluoroacetimidohydrazides for the Synthesis of 2‐(5‐Trifluoromethyl‐1,2,4‐triazol‐3‐yl)anilines

Chen

Liu

et al. 2022

Adv Synth Catal

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A copper-catalyzed intramolecular decarbonylative cyclization reaction of isatins and trifluoroacetimidohydrazides for the synthesis of 2-(5trifluoromethyl-1,2,4-triazol-3-yl)aniline derivatives has been developed. This transformation proceeds through a cascade condensation, hydrolysis, decarboxylation, and intramolecular CÀ N bond formation sequence. The obtained 1,2,4-triazole products bearing a free amino group can be readily converted into other useful compounds.

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Development of Cyanopyridazine Derivatives as Photoredox Catalysts and Evaluation of their Catalytic Performance

Tang,

Liu,

Zhu

et al. 2024

Adv Synth Catal

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An array of cyanopyridazine derivatives have been developed through a sequence of (3+3) cycloaddition/oxidative aromatization/derivatization steps. Investigation of the physicochemical properties of these compounds shows that four have interesting fluorescence properties and have the potential to be developed into bimodal photoredox catalysts. One has been confirmed to be an photoredox catalyst in the reactions of N‐aryl‐tetrahydroisoquinolines with phosphite, nitromethane, malonitrile and sodium thiocyanate, led to 22%‐95% yields. The catalyst capabilities remain with recyclable using under the reaction conditions.

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

Abstract: 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. Notable advantages of the reaction...

Cited by 27 publications

References 49 publications

Trifluoromethylated Amidrazone Derivatives as Key Compounds for the Synthesis of 4-Aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles

Trifluoromethylated Amidrazone Derivatives as Key Compounds for the Synthesis of 4-Aryl-3,5-bis(trifluoromethyl)-4H-1,2,4-triazoles

Copper‐Catalyzed Decarbonylative Cyclization of Isatins and Trifluoroacetimidohydrazides for the Synthesis of 2‐(5‐Trifluoromethyl‐1,2,4‐triazol‐3‐yl)anilines

Development of Cyanopyridazine Derivatives as Photoredox Catalysts and Evaluation of their Catalytic Performance

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