Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 10002 - 10007
Published: Nov. 14, 2024
Menadione and its structural analogues are important motifs present in various bioactive natural products drugs with a wide range of biological activities. In addition, β-trifluoromethyl enone has been employed as an efficient fluorinated building block for the synthesis CF
Language: Английский
International Journal of Molecular Sciences, Journal Year: 2025, Volume and Issue: 26(5), P. 2114 - 2114
Published: Feb. 27, 2025
Malaria remains a major global health problem that has been exacerbated by the impact of COVID-19 pandemic on systems. To combat this, World Health Organization (WHO) set target driving forward research into innovative treatment methods such as new drugs and vaccines. Quinones, particularly 1,4-naphthoquinones, have identified promising candidates for development antiprotozoal drugs. Herein, we report several preparation 2-benzyl-1,4-naphthoquinones. In particular, silver-catalyzed Kochi-Anderson radical decarboxylation is well suited these compounds. The activity all synthesized compounds was evaluated against Plasmodium falciparum NF54 Trypanosoma brucei rhodesiense STIB900. Cytotoxicity towards L6 cells also determined, respective selectivity indices (SI) were calculated. exhibited good antiplasmodial P. (NF54) strain, (2-fluoro-5-trifluoromethylbenzyl)-menadione 2e, which showed strong efficacy high (IC50 = 0.006 µM, SI 7495). addition, displayed favorable physicochemical properties, suggesting benzylnaphthoquinone scaffold may be viable option
Language: Английский
Citations
1
Organic & Biomolecular Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Jan. 1, 2025
This review summarizes recent progress in EDA complex-promoted C–S bond formation using various sulfur-containing substrates under mild conditions via visible light irradiation.
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: 90(6), P. 2214 - 2229
Published: Jan. 30, 2025
The selective oxidative cleavage and functionalization of C(OH)–C bonds in tertiary alcohols harbor immense feasibility organic synthesis enable the production high value-added chemicals from renewable biomass. However, it remains a challenge, owing to inherent kinetic inertness thermodynamic stability lack Cα–H. Taking huge potential challenge bond activation into consideration, herein, we show first example an inexpensive bifunctional ferric nitrate catalyst for catalytic direct oxidation structurally distinct esters with environmentally benign molecular oxygen as oxidant MeOH solvent, without assistance any additives. Detailed mechanistic studies reveal that this tandem process is initiated by synergistic effects iron ion ion, which serve Lewis acids dehydrating nitrogen dioxide radical precursor inducing cleavage, respectively.
Language: Английский
Citations
0
The Journal of Organic Chemistry, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 5, 2025
An electrooxidative C-C coupling between arylhydrazines and aminoquinones has been developed for the construction of aryl-substituted aminoquinones, which features excellent chemo- regioselectivity. Mechanistic studies support idea that denitrogenative formation aryl radicals might be involved in metal-free C-H arylation.
Language: Английский
Citations
0
Organics, Journal Year: 2025, Volume and Issue: 6(1), P. 9 - 9
Published: Feb. 14, 2025
A series of photoacylations 1,4-naphthoquinone with various aldehydes and using Pyrex-filtered UVB light was conducted under continuous-flow conditions. Acetone served as a triplet photosensitizer convenient solvent that kept all materials in solution could be easily removed. The corresponding acylated 1,4-naphthohydroquinone photoproducts were obtained acceptable to excellent yields 30–90% residence times just 70 min. photoacylation process successfully coupled in-line oxidation obtain 1,4-naphthoquinones.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2025, Volume and Issue: unknown
Published: Feb. 17, 2025
We reported an unprecedented chalcogen element (Se, S) insertion reaction with functionalized aminomaleimide to assemble medium-sized nitrogen-containing organic selenium/sulfur catalyzed by bases. During these [5/6 + 1] tandem annulations, a variety of low-valent inorganic chalcogenides exhibited excellent compatibility, providing wide scope structurally diverse 1,4-selenazepanes (17 examples, 60–71% yields), 1,4-benzothiazepines (20 74–86% and 1,4-thiazines (6 31–68% yields). The characteristics this transformation are high atomic economy, formation two C–Se or C–S bonds in one step, avoiding the use unstable toxic reagents under mild conditions.
Language: Английский
Citations
0
Molecules, Journal Year: 2024, Volume and Issue: 29(24), P. 5920 - 5920
Published: Dec. 15, 2024
A series of [2+2]-photocycloadditions 1,4-naphthoquinone with various alkenes and diphenylacetylene were investigated under batch continuous-flow conditions. Acetone-sensitization furnished the corresponding photoadducts in good to excellent yields purities. Compared operations that demanded exhaustive irradiation times 10–13 h, flow process generally gave superior conversions subsequently a residence time just 60 min. The structures several photoaddition products further determined by crystal structure analysis.
Language: Английский
Citations
1
The Chemical Record, Journal Year: 2024, Volume and Issue: unknown
Published: Nov. 19, 2024
Organic sulfur compounds encompass a vast and diverse variety of species that possess unique biological activity due to the presence atoms or sulfur-containing functional groups. These are widely present in natural products, pharmaceuticals, agricultural chemicals, materials. In recent years, numerous such as thiols, thioethers, disulfides, thiourea, dimethyl sulfoxide, sulfonates their derivatives, well inorganic compounds, have been utilized coupling agents synthesize (hetero)aryl sulfides via C-H Functionalization. novel transformations provide effective methods for constructing C-S bond (hetero)arenes, while also expanding scope with potential activity. Therefore, synthesis aryl through functionalization has attracted widespread attention. This review mainly focuses on construction since 2015. We hope this offers useful conceptual overview inspires further advancements efficient bonds.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2024, Volume and Issue: 26(45), P. 9682 - 9688
Published: Nov. 5, 2024
Regioselective reactions of biologically significant quinones are challenging. An unprecedented advancement in quinone monoacetal (QMA) chemistry is proposed for constructing regioselective and less explored α-alkylated QMAs through the Morita–Baylis–Hillman (MBH) reaction. Electrophilic were transformed to nucleophilic umpolung reagents aldol-type condensation with several electrophiles. Mechanistic studies reveal that solvent (TFE:water (1:1)) situ-generated potassium acetate accelerate The ensuing MBH adducts scalable underwent post-synthetic transformations late-stage functionalization.
Language: Английский
Citations
0
Organic Letters, Journal Year: 2024, Volume and Issue: 26(46), P. 10002 - 10007
Published: Nov. 14, 2024
Menadione and its structural analogues are important motifs present in various bioactive natural products drugs with a wide range of biological activities. In addition, β-trifluoromethyl enone has been employed as an efficient fluorinated building block for the synthesis CF
Language: Английский
Citations
0