Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

Nemoto, Koji; Tanaka, Shinya; Konno, Megumi; Onozawa, Satoru; Chiba, Masakatsu; Tanaka, Yuuki; Sasaki, Yosuke; Okubo, Ryo; Hattori, Tetsutaro

doi:10.1016/j.tet.2015.12.028

Cited by 47 publications

(34 citation statements)

References 65 publications

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“…The equilibrium between 44, 48,a nd 50 is proposed to lie significantly towardt he starting materials, the equilibrium being displaced by the carboxylation under high pressureo fC O 2 .N otably,H Cl may be eliminated from zwitterionic species 48 to form indolylaluminum species 51 instead of ate complex 50. [30] Inglesona nd co-workers reportedt hat treatment of 1-methylindole 44 with AlCl 3 at 80 8Ca fforded zwitterionic species similar to adduct 48,a se videnced by X-ray analysis. [31] The same treatment of thiophenes and benzothiophenes with EtAlCl 2 under pressurized CO 2 gave the corresponding carboxylic acids in up to 90 %yield.…”

Section: Lewis-acid-mediated Carboxylationmentioning

confidence: 93%

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

2017

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Carbon dioxide (CO2) represents the most abundant and accessible carbon source on Earth. Thus the ability to transform CO2 into valuable commodity chemicals through the construction of C−C bonds is an invaluable strategy. Carboxylic acids and derivatives, the main products obtained by carboxylation of carbon nucleophiles by reaction of CO2, have wide application in pharmaceuticals and advanced materials. Among the variety of carboxylation methods currently available, the direct carboxylation of C−H bonds with CO2 has attracted much attention owing to advantages from a step‐ and atom‐economical point of view. In particular, the prevalence of (hetero)aromatic carboxylic acids and derivatives among biologically active compounds has led to significant interest in the development of methods for their direct carboxylation from CO2. Herein, the latest achievements in the area of direct C−H carboxylation of (hetero)aromatic compounds with CO2 will be discussed.

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Section: Lewis-acid-mediated Carboxylationmentioning

confidence: 93%

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

2017

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“…TH5-61-1 (138.1 mg) was separated by preparative HPLC (35–80% MeOH) to produce 4-hydroxybenzoic acid ( 10 , 17.1 mg) [50], 3-(2-hydroxyphenyl)acrylic acid ( 11 , 70 mg) [52], and salicylic acid ( 12 , 10.9 mg) [53]. TH5-57-5 (50.9 mg) was separated by preparative HPLC (25–85% MeOH) to produce 1H-indole-3-carboxylic acid ( 9 , 4.1 mg) [54]. The structure of the 14 phenolic compounds isolated from A. argyi was characterized by NMR and ESI-MS analyses.…”

Section: Methodsmentioning

confidence: 99%

Protective Effect of Phenolic Compounds Isolated from Mugwort (Artemisia argyi) against Contrast-Induced Apoptosis in Kidney Epithelium Cell Line LLC-PK1

et al. 2019

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We investigated whether 14 phenolic compounds isolated from Artemisia argyi could prevent the apoptotic damage caused by iodixanol, an iodinated contrast agent, on LLC-PK1 cells. Iodixanol was used to induce cytotoxicity in LLC-PK1 cells. Apoptotic cell death was observed as the fluorescence intensity emitted by annexin V and Hoechst 33342 stains. Western blotting was used to detect specific proteins. Seven phenolic compounds protected against iodixanol-induced LLC-PK1 cell death in a concentration-dependent manner. Among them, methyl caffeate exerted the strongest protective effect, and co-treatment with 50 and 100 μM methyl caffeate decreased intracellular reactive oxygen species elevated by 25 mg/mL iodixanol. In addition, the treatment of LLC-PK1 cells with iodixanol resulted in an increase in apoptotic cell death, which decreased by co-treatment with methyl caffeate. Iodixanol caused a cytotoxicity-related increase in the phosphorylation of extracellular-signal-regulated kinase, c-Jun N-terminal kinase, and P38; and a similar increase in the expression levels of kidney injury molecule-1 and cleaved caspase-3. However, the up-regulation of these proteins was reversed by co-treatment with methyl caffeate. These findings suggest that phenolic compounds isolated from A. argyi play an important role in protecting kidney epithelium cells against apoptotic damage caused by iodixanol.

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“…Synthetic application has also been performed with substrate 2p to make electron‐rich aromatic moieties. 1‐Ethyl‐2‐(4‐methoxyphenyl)‐5‐phenyl‐benzo[ d ]imidazole ( 5 ) was obtained in 85 % yield by following standard Suzuki reaction using PhB(OH) 2 (Figure b). Similarly, Sonogashira reaction was performed so synthesize 1‐ethyl‐2‐(4‐methoxyphenyl)‐5‐( p ‐tolylethynyl)‐benzo[ d ]imidazole 6 in 80 % yield.…”

Section: Resultsmentioning

confidence: 99%

Intramolecular C(sp³)–H Imination towards Benzimidazoles Using Tetrabutylammonium Iodide and tBuOOH

Bose

Mal

2019

Eur J Org Chem

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Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

Cited by 47 publications

References 65 publications

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

Protective Effect of Phenolic Compounds Isolated from Mugwort (Artemisia argyi) against Contrast-Induced Apoptosis in Kidney Epithelium Cell Line LLC-PK1

Intramolecular C(sp³)–H Imination towards Benzimidazoles Using Tetrabutylammonium Iodide and tBuOOH

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Me2AlCl-mediated carboxylation, ethoxycarbonylation, and carbamoylation of indoles

Cited by 47 publications

References 65 publications

C−H Carboxylation of Aromatic Compounds through CO2 Fixation

C−H Carboxylation of Aromatic Compounds through CO2 Fixation

Protective Effect of Phenolic Compounds Isolated from Mugwort (Artemisia argyi) against Contrast-Induced Apoptosis in Kidney Epithelium Cell Line LLC-PK1

Intramolecular C(sp3)–H Imination towards Benzimidazoles Using Tetrabutylammonium Iodide and tBuOOH

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Product

Resources

About

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

C−H Carboxylation of Aromatic Compounds through CO₂ Fixation

Intramolecular C(sp³)–H Imination towards Benzimidazoles Using Tetrabutylammonium Iodide and tBuOOH