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Relevant academic research and scientific papers

First Aminocatalytic Synthesis of Bis(indolyl)methanes and DFT Studies on the Reaction Pathway

Abstract: Carbon–carbon bond-formation by aminocatalytic nucleophilic addition to aryl aldehyde ideally generates addition–elimination product. Here, we report an unexpected, yet efficient aminocatalytic nucleophilic addition of indole to aryl aldehydes t

Palladium-catalyzed carbonylative bis(indolyl)methanes synthesis with TFBen as the CO source

An efficient and convenient palladium-catalyzed carbonylative procedure for the synthesis of bis(indolyl)methanes has been established for the first time. With TFBen (benzene-1,3,5-triyl triformate) as the solid CO source, aryl iodides and indoles were tr

Synthesis of bis(indolyl)methane derivatives catalyzed by recyclable nano Fe3O4@ZrO2/SO42-

Background: Bis(indolyl)methane derivatives exhibit varied biological and pharmacological properties like fantibacterial and antiangiogenic activities, acting as cytotoxic agents and tumor growth inhibitors. Several approaches of bis(indolyl)methane synth

Visible-light-mediated anti-regioselective nitrone 1, 3-dipolar cycloaddition reaction and synthesis of bisindolylmethanes

The development of photoredox reactions of 1, 3- dipolar cycloaddition of nitrones with alkenes is reported. It offers an efficient synthetic method to obtain isoxazolidine derivatives under mild conditions in synthetically useful yields. The nitrones are cyclized with oxidizable styrenes and aliphatic alkenes via a polar radical crossover cycloaddition reaction through photocatalytic reaction without additives. In addition, bis(indole)methanes can also be prepared through this method.

Poly-substituted bis-indolymethane derivative and preparation method thereof

The invention relates to a poly-substituted bis-indolymethane derivative and a preparation method thereof. The structural formula of the derivative is as shown in a formula (I) in the specification, R refers to substituted aryl or alkyl, R refers to alkoxy, halogen or alkyl, the substituted aryl comprises phenyl and naphthyl, and the alkyl comprises methyl, ethyl and cyclohexyl. The preparation method includes the steps: dissolving a nitrone derivative as shown in a formula (II), an indole structure compound as shown in a formula (III) and a photocatalyst as shown in a formula (IV) in an organic solvent under nitrogen atmosphere at room temperature; uniformly mixing the materials; illuminating mixture under blue LEDs (light-emitting diodes) lamps (or other visible light sources such as incandescent lamps) for a few hours; performing rotary evaporation on the solvent after complete reaction; performing chromatographic separation and purification by a silica gel column to obtain the poly-substituted bis-indolymethane derivative. The preparation method solves the problems that an existing bis-indolymethane derivative needs a transitional metal catalysis system in synthesis, yield is low, and an existing method is poor in environmental protection property. Reaction conditions are mild, the method is simple, operation is convenient, and yield is high.

Exploration of Aberrant Behaviour of Grignard Reagents with Indole-3-carboxaldehyde: Application to the Synthesis of Turbomycin B and Vibrindole A Derivatives

An aberrant reaction of Grignard reagents with N-alkylated indole-3-carboxaldehyde has been observed. Contrary to the usual formation of an alcohol, it afforded an unusual bis(indolyl)methane product. A systematic study on this new mode of reactivity and its application to a synthesis of the potent antibiotic turbomycin B and vibrindole A derivatives is reported.

Tunable titanocene lewis acid catalysts for selective friedel-crafts reaction of indoles and N-sulfonylaldimines

A newc strategy to control the selective Friedel-Crafts reaction of indoles and imines under mild conditions was developed. Phenol derivatives were established as efficient ligands to finely tune the activity of titanocene dichloride. Cp2TiCl2 and phenol catalyzed the mono-Friedel-Crafts reaction of indoles and N-sulfonyl aldimines with good yields (91 %), whereas o-aminophenol significantly enhanced the activity of the titanocene catalyst and promoted the synthesis of bisindole with excellent yields (98 %). The new organometallic Lewis acid catalysts are air-tolerant, can be used with low catalyst loading (3 mmol-%) and are compatible with -NO2, -F, -Cl, -Br, and -OMe (30 examples with yields from good to excellent). The titanocene catalysts were fully characterized by NMR and HRMS analysis. The results suggest that Cp2TiCl(OC6H5) (I) and Cp2TiCl(OC6H4NH3+Cl-) (II) were catalytic species for the mono- and double-Friedel-Crafts reactions, respectively. Distinguished from single functional acid catalysts I, catalyst II showed a catalytic cooperative effect of two acid components, which led to a fine tuning of the reactivity as well as to the selectivity of the desired reaction pathways. A Ti-catalyzed, highly selective Friedel-Crafts reaction of indoles and imines has been developed. Cp2TiCl2 and phenol, with a single Lewis acid site, catalyzed the mono-Friedel-Crafts reaction of indoles and N-sulfonylaldimines, whereas o-aminophenol enhanced the acidity of titancene catalyst, enabling both Lewis and Bronsted acid sites to promote the synthesis of bisindole.

Highly modulated bisindoles: ligands for copper-catalyzed Sonogashira reaction

Bisindoles (BIMs) were modulated as powerful N,N′ donor ligands for the copper-catalyzed Sonogashira reaction. Ligand screening experiments on 11 BIM compounds found that 3,3′-(4-chlorophenyl)methylenebis(1-methyl-1H-indole) (10%) efficiently accelerated CuCl (5%)-catalyzed cross-coupling of aryl iodides with terminal alkynes. A wide range of substituted aryl iodides and/or alkyl- and aryl-substituted terminal alkynes were examined, leading to the corresponding coupling products with yields up to 99%. An efficient and scalable protocol for the synthesis of BIM ligands on a gram scale, with extremely low catalyst loading of o-ClC6H4NH3 +Cl?, was also developed with a reaction time of 20?min with yields up to 93%. This novel N,N′ ligand was air-stable, easily available and highly modulated with low copper loading. Copyright

One-pot total synthesis of streptindole, arsindoline B and their congeners through tandem decarboxylative deaminative dual-coupling reaction of amino acids with indoles

This paper described a decarboxylative deaminative dual-coupling reaction of amino acids with indoles to afford BIM scaffolds and its further application to the one-pot total synthesis of natural products. This method featured a stimulating example of activating amino acids in one pot as multi-carbon building blocks for transformation into final targets which are equipped with amino acid side chain backbones. This journal is

A stereoselective Povarov reaction leading to exo-tetrahydroindolo[3,2-c] quinoline derivatives catalyzed by iodine

We report an iodine-catalyzed Povarov reaction using indole as dienophile carried out in toluene at room temperature. This three-component reaction, coupling an aldehyde, an amine, and an indole, proved to be an efficient method for synthesizing exo-indol