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Relevant academic research and scientific papers

Pyridinium tribromide catalyzed condensation of indoles and aldehydes to form bisindolylalkanes

An efficient synthetic method for bis(indol-3-yl)alkane derivatives has been developed. In the presence of 5 mol% of pyridinium tribromide (PTB), the condensation of indoles and aldehydes proceeded smoothly under mild conditions, giving rise to the corresponding bis(indol-3-yl)alkanes in good to excellent yields.

A practical synthesis of bis(indolyl)methanes employing boric acid

A variety of aldehydes and ketones react rapidly with indoles in the presence of boric acid under solvent-free conditions to afford the corresponding bis(indolyl)methanes. Excellent yields and short reaction times together with the environmentally friendly nature of boric acid make this procedure useful and attractive to produce a variety of bis(indolyl)methanes. The use of boric acid makes it quite simple, more convenient, and practical. This new method offers several advantages such as high conversions, cleaner reaction profiles, short reaction times, and the use of inexpensive and readily available boric acid. Springer-Verlag 2010.

Nitro-substituted 3,3′-bis(indolyl)methane-modified silica gel as a sorbent for solid-phase extraction of flavonoids

A novel solid-phase extraction (SPE) sorbent was synthesized by chemical immobilization of nitro-substituted 3,3′-bis(indolyl)methane onto pure silica. The nitro-substituted 3,3′-bis(indolyl)methane-modified silica was evaluated by elemental analysis (EA) and Fourier transform infrared spectroscopy (FT-IR). Coupled to high performance liquid chromatography (HPLC), the extraction performance of the sorbent was evaluated by using five flavonoids as model analytes. The results showed that the new sorbent could offer multiple intermolecular interactions, such as π-π, hydrophobic, and hydrogen bonding interactions. Several factors including the extraction material, sample solution pH, sample loading rate, eluent type, volume of eluent, elution rate, and volume of sample loading were optimized. Under the optimal conditions, the proposed method was applied for the analysis of five flavonoids in grape juice. Satisfactory linear ranges for flavonoids were obtained in the range of 10-200 ng mL-1 for myricetin, 5-200 ng mL-1 for quercetin and apigenin, and 1-200 ng mL-1 for luteolin and kaempferol, with correlation coefficients (R) ranging from 0.9908 to 0.9996. Limits of detection (LODs) were in the range of 0.5-10 ng mL-1. The recovery values of spiked grape juice ranged from 91.5% to 120.7% with relative standard deviations (RSDs) less than 9.12% (n = 5). As a novel solid-phase extraction sorbent, the nitro-substituted 3,3′-modified silica exhibited a higher extraction efficiency towards the tested compounds than diol-modified silica.

Utilization of flow chemistry in catalysis: New avenues for the selective synthesis of Bis(indolyl)methanes

Flow chemistry enables the preparation of bis(indolyl)methanes from various indoles and structurally divergent aldehydes using Sc(OTf)3 catalysis. The reaction is regioselective for C-3 functionalization of the indoles, occurring over short reaction times allowing for rapid investigation of scope with straightforward work up facilitating product isolation.

Bis-indolylation of aldehydes and ketones using silica-supported FeCl3: Molecular docking studies of bisindoles by targeting SARS-CoV-2 main protease binding sites

We report herein an operationally simple, efficient and versatile procedure for the synthesis of bis-indolylmethanes via the reaction of indoles with aldehydes or ketones in the presence of silica-supported ferric chloride under grindstone conditions. The prepared supported catalyst was characterized by SEM and EDX spectroscopy. The present protocol has several advantages such as shorter reaction time, high yield, avoidance of using harmful organic solvents during the reaction and tolerance of a wide range of functional groups. Molecular docking studies targeted toward the binding site of SARS-CoV-2 main protease (3CLpro or Mpro) enzymes were investigated with the synthesized bis-indoles. Our study revealed that some of the synthesized compounds have potentiality to inhibit the SARS-CoV-2 Mpro enzyme by interacting with key amino acid residues of the active sites via hydrophobic as well as hydrogen bonding interactions.

Facile access to bis(indolyl)methanes by copper-catalysed alkylation of indoles using alcohols under air

Bis(3-indolyl)methanes (BIM) are important and present in the structure of many alkaloid and bioactive compounds (anti-inflammatory, anticancer, antiobesity, antimicrobial, etc.). Herein, we have reported an air stable and convenient Cu(OAc)2 c

Phosphine-Free Manganese(II)-Catalyst Enables Acceptorless Dehydrogenative Coupling of Alcohols with Indoles

Herein, an air-stable, molecularly defined NNN?Mn(II) pincer complex catalyzed acceptorless dehydrogenative coupling of alcohols with indoles is reported. A wide variety of symmetrical and unsymmetrical bis(indolyl)methane derivatives as well as some structurally important products such as Vibrindole A, Turbomycin B alkaloid, Antileukemic, and Anticancer agents were synthesized. Mechanistic studies illustrate the importance of the NH moiety in the complex and the crucial role of metal-ligand cooperation during catalysis. (Figure presented.).

Sulfonated Tetraphenylethylene-Based Hypercrosslinked Polymer as a Heterogeneous Catalyst for the Synthesis of Symmetrical Triarylmethanes via a Dual C-C Bond-Cleaving Path

A sulfonic acid functionalized tetraphenylethylene-based hypercrosslinked polymer (THP-SO 3H) with a well-developed porous network and accessible sulfonic acid sites was synthesized and characterized by different analytical techniques. The cata

Bimetallic Metal Organic Frameworks as Magnetically Separable Heterogeneous Catalysts and Photocatalytic Dye Degradation

A new bimetallic MOF (BMOF) has been synthesized using iron and zinc as inorganic metal nodes and 1,4-benzenedicarboxylic acid (BDC) as the organic linker molecule. BMOF was confirmed by single-crystal X-ray diffraction (SCXRD), X-ray photoelectron spectroscopy (XPS), transmission electron microscopy high-angle annular dark-field imaging (TEM-HAADF), field emission scanning electron microscopy energy-dispersive X-ray analysis (FESEM-EDX), vibrating sample magnetometry (VSM) and inductively coupled plasma mass spectrometry (ICP-MS) analysis. The synthesized BMOF shows excellent optical and magnetic properties. BMOF acts as a heterogeneous catalyst and shows high catalytic activity towards bis(indolyl)methane synthesis and photocatalytic degradation of methylene blue (MB) under visible-light illumination.

A facile iron-catalyzed dual C-C bond cleavage: An approach towards triarylmethanes

A facile iron-catalyzed dual C-C bond cleaving reaction involving 1,3-dicarbonyl units along with electron-rich and sterically bulky arenes as efficient carbon-based leaving groups has been developed. The scope of the dual C-C bond breaking reaction was s