First synthesis of functionalized 5-aryl-3-(trifluoromethyl)phenols by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-aryl-3-silyloxy-1-trifluoromethyl-2-en-1-ones

Büttner, Stefan; Riahi, Abdolmajid; Hussain, Ibrar; Yawer, Mirza Arfan; Lubbe, Mathias; Villinger, Alexander; Reinke, Helmut; Fischer, Christine; Langer, Peter

doi:10.1016/j.tet.2008.12.076

Cited by 19 publications

(12 citation statements)

References 40 publications

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“…We were focusing on ligands possessing the electron-withdrawing trifluoromethyl (-CF 3 ) group and various electron donating aryl groups. The -CF 3 group is known to play an important role in drug-receptor interactions, it enhances the lipophilicity of such compounds which can result in improved cellular uptake in comparison to their methyl substituted analogues 17,18 and increased cytotoxicity. 19 On the other side of a diketonate scaffold, aromatic ring systems were used as substituents: the smallest are five-membered rings (2-furyl and 2thienyl), phenyl and 4-chlorophenyl are representatives of six-membered rings, whereas 2-naphthyl and benzodioxolyl are polycyclic aromatic systems.…”

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confidence: 99%

Structure-Related Mode-of-Action Differences of Anticancer Organoruthenium Complexes with β-Diketonates

et al. 2015

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A series of organoruthenium(II) chlorido complexes with fluorinated O,O-ligands [(η(6)-p-cymene)Ru(F3C-acac-Ar)Cl] (1a-6a) and their respective 1,3,5-triaza-7-phosphaadamantane (pta) derivatives [(η(6)-p-cymene)Ru(F3C-acac-Ar)pta]PF6 (1b-6b) were synthesized and fully characterized in both solution and solid state. All complexes were inactive against nonmalignant keratinocytes but displayed variable activity against cancer cell models (ovarian, osteosarcoma). Compounds with a ligand containing the 4-chlorophenyl substituent (6a and 6b) exhibited the strongest anticancer effects. Despite a marginally lower cellular Ru accumulation compared to the chlorido complexes, pta analogues showed higher activity especially in the osteosarcoma model. Reduction of glutathione levels by buthionine sulfoximine (BSO) significantly enhanced the activity of all compounds with the most pronounced effects being observed for the pta series resulting in IC50 values down to the nanomolar range. While all chlorido complexes potently induce reactive oxygen species, DNA damage, and apoptosis, the respective pta compounds widely lacked ROS production but blocked cell cycle progression in G0/G1 phase.

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confidence: 99%

Structure-Related Mode-of-Action Differences of Anticancer Organoruthenium Complexes with β-Diketonates

et al. 2015

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“…The starting 1,3-diketones 2a , 2b , and 2c , previously used for pyrazoline ring formation, 49 were obtained from the corresponding bromine-substituted acetophenones by Claisen condensation with ethyl trifluoroacetate in almost quantitative yields. 50 The reaction of 4-fluorophenyl azide 1 with 1-(3-bromophenyl)-4,4,4-trifluorobutane-1,3-dione 2b yielded in 1,2,3-triazole 3b . However, in triethylamine solution, the reaction was faster and the target triazole was isolated pure from the reaction mixture by simple filtration.…”

Section: Results and Discussionmentioning

confidence: 99%

Exciplex-Forming Systems of Physically Mixed and Covalently Bonded Benzoyl-1H-1,2,3-Triazole and Carbazole Moieties for Solution-Processed White OLEDs

et al. 2022

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Using the newly designed exciplex-forming 1,2,3-triazole-based acceptors with fast and efficient singlet → triplet intersystem crossing (ISC) processes, carbazole and benzoyl-1 H -1,2,3-triazole derivatives were synthesized by Dimroth-type 1,2,3-triazole ring formation and Ullmann–Goldberg C–N coupling reactions. Due to the exciplex formation between covalently bonded electron-donating (carbazole) and 1,2,3-triazole-based electron-accepting moieties with small singlet-triplet splitting (0.07–0.13 eV), the compounds exhibited ISC-assisted bluish–green thermally activated delayed fluorescence. The compounds were characterized by high triplet energy levels ranging from 2.93 to 2.98 eV. The most efficient exciplex-type thermally activated delayed fluorescence was observed for ortho-substituted carbazole-benzoyl-1 H -1,2,3-triazole which was selected as a host in the structure of efficient solution-processed white light-emitting diodes. The best device exhibited a maximum power efficiency of 10.7 lm/W, current efficiency of 18.4 cd/A, and quantum efficiency of 7.1%. This device also showed the highest brightness exceeding 10 thousand cd/m 2 . Usage of the exciplex-forming host allowed us to achieve a low turn-on voltage of 3.6 V. High-quality white electroluminescence was obtained with the close to nature white color coordinates (0.31, 0.34) and a color rendering index of 92.

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“…With the optimal conditions established, we prepared various trifluoromethyl-β-diketones 1a-t, according to known procedures. 21 We then subjected each to the reaction conditions (MC, tBuOK 10 mol%, neat, 80 o C) ( Table 2). Excellent regioselectivity is observed in the crude.…”

Section: Resultsmentioning

confidence: 99%

A solvent-free, base-catalyzed domino reaction towards trifluoromethylated benzenes from bio-based methyl coumalate

et al. 2018

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A novel, efficient, and environmentally compatible method for CF3-substituted benzene production is reported. It sources a bio-based feedstock, employs tBuOK as catalyst, and is solvent-free. This regioselective approach provides various trifluoromethyl benzenes in good to excellent yields, without extra oxidant or special care. CO2 and water are the only byproducts of this process, and reaction conditions can scale up to gram quantities. The transformation involves an unprecedented tBuOK-catalyzed domino process, and features Michael addition / 6π-electrocyclic ring opening / [1,5]-H shift / carba-6π-electrocyclic ring closure / decarboxylative aromatization reactions.

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First synthesis of functionalized 5-aryl-3-(trifluoromethyl)phenols by regioselective [3+3] cyclocondensations of 1,3-bis(silyloxy)-1,3-butadienes with 3-aryl-3-silyloxy-1-trifluoromethyl-2-en-1-ones

Cited by 19 publications

References 40 publications

Structure-Related Mode-of-Action Differences of Anticancer Organoruthenium Complexes with β-Diketonates

Structure-Related Mode-of-Action Differences of Anticancer Organoruthenium Complexes with β-Diketonates

Exciplex-Forming Systems of Physically Mixed and Covalently Bonded Benzoyl-1H-1,2,3-Triazole and Carbazole Moieties for Solution-Processed White OLEDs

A solvent-free, base-catalyzed domino reaction towards trifluoromethylated benzenes from bio-based methyl coumalate

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