Condition-controlled selective synthesis of coumarins and flavones from 3-(2-hydroxyphenyl)propiolates and iodine

2H-Chromen-2-ones (coumarins) and 4H-chromen-4-ones (flavones) were selectively prepared via the reaction of 3-(2-hydroxyphenyl)propiolates with iodine in toluene and N,N-dimethylformide, respectively.     

Surfactant-assisted synthesis of bis(indolyl)methanes in water

An environmentally friendly synthesis method for bis(indolyl)methanes has been developed in the presence of sodium lauryl ether sulfate(SLES),electrophilic substitution reactions of indoles with aldehydes were accomplished in water as solvent at room temperature without any Bronested or Lewis acid catalysts.     

Ionic liquid promoted synthesis of bis(indolyl) methanes

1-benzyl-3-methyl imidazolium hydrogen sulphate [bnmim][HSO₄] was found to be an effective catalyst for the condensation reaction of indoles and derivatives with benzaldehydes in microwave irradiation with lower reaction time and higher yields to give bis(indolyl) methanes.      

A versatile and practical synthesis of bis(indolyl)methanes/bis(indolyl)glycoconjugates catalyzed by trichloro-1,3,5-triazine

A practical and efficient electrophilic substitution reaction of indoles with a variety of aldehydes was carried out using catalytic trichloro-1,3,5-triazine (10 mol %) in acetonitrile to furnish the corresponding bis(indolyl)methanes in excellent yields. Similarly, sugar derived aldehydes gave hitherto unknown bis(indolyl)glycoconjugates in very good yields.     

Eutectic salts promote green synthesis of bis(indolyl) methanes

A convenient and rapid method for the electrophilic substitution reaction of indoles with carbonyl compounds has been developed by using deep eutectic solvent as green and reusable catalysts to afford the corresponding bis(indolyl) methanes in excellent yields at room temperature under mild reaction conditions.     

A mild synthesis of bis(indolyl)methanes using a deep eutectic solvent

Deep eutectic solvents (such as the combination of urea and choline chloride) are effective solvents/organocatalysts for the condensation of indole and aryl or alkenyl aldehydes to form bis(indolyl)methanes. The reaction conditions are quite mild and do not require additional Bronsted or Lewis acid catalyst, though they fail with ketones or aliphatic aldehydes. Given the inexpensive, non-toxic, and recyclable nature of the DES, these reaction conditions are simple and highly environmentally friendly.     

Tetrabutylammonium tribromide as efficient catalyst in the synthesis of bis(indolyl)methanes

An efficient procedure has been developed for the synthesis of bis(indolyl)methane derivatives by condensation of aldehydes with indole in the presence of tetrabutylammonium tribromide as catalyst.     

Molecular iodine-catalyzed efficient and highly rapid synthesis of bis(indolyl)methanes under mild conditions

Highly rapid and efficient electrophilic substitution reactions of indoles with various aldehydes and ketones were carried out using I₂ in CH₃CN to afford the corresponding bis(indolyl)methanes in excellent yields.     

Efficient synthesis of bis(indolyl)methanes,bispyrazoles and biscoumarins using 4-sulfophthalic acid

Research on Chemical Intermediates - 4-Sulfophthalic acid (4-H3SPA) solution 50 wt% in H2O has been effectively catalyzed the synthesis of a series of biologically relevant...     

An effective lactic acid-modified Hβ zeolite for synthesis of bis(indolyl)methanes

Excellent activity and stability have been observed for a lactic acid-modified Hβ (LA-Hβ) zeolite in the synthesis of bis(indolyl)methanes by Friedel–Crafts alkylation of indole with aldehydes. It is proposed that lactic acid treatment is appropriate for dealumination of Hβ zeolite, and results in a LA-Hβ zeolite with greater surface area, fewer weak acid sites, and more moderately-strong acid sites, as confirmed by the Brunauer–Emmett–Teller method, inductively coupled plasma emission spectrometry, and temperature-programmed desorption of NH₃. Moreover, both electronic and steric effects of substituents on the aromatic ring of the aldehydes were found to be important in this reaction.     

Gallium(III) halide-catalyzed coupling of indoles with phenylacetylene: synthesis of bis(indolyl)phenylethanes

Indoles undergo smooth coupling with phenylacetylene in the presence of 10 mol % of gallium(III) chloride or gallium(III) bromide under mild conditions to afford the corresponding 1,1-bis(1H-3-indolyl)-1-phenylethanes in high yields and with high selectivity.     

温和条件下丁二酰亚胺-N-磺酸催化合成双吲哚甲烷和香豆素衍生物(英文)

A mild and simple procedure is described for the synthesis of bis(indolyl)methane and coumarin derivatives using succinimide-N-sulfonic acid as an efficient,cheap,and reusable catalyst under mild conditions.     

An eco-friendly procedure for the efficient synthesis of bis(indolyl)methanes in aqueous media

A new, convenient and high yielding procedure for the preparation of bis(indolyl)methanes in water by electrophilic substitution reaction of indoles with different carbonyl compounds in the presence of a catalytic amount of [Cu(3,4-tmtppa)](MeSO₄)₄ (1 mol%) as a highly stable and reusable catalyst is described. This procedure has also been applied successfully for the preparation of bis(pyrazole-5-ols) and dipyrromethanes.     

Iron(III)(salen)Cl as an efficient catalyst for synthesis of bis(indolyl)methanes

[Fe(III)(salen)]Cl (salen = N,N′-ethylenebis(salicylimine)) is an efficient catalyst for the electrophilic substitution of indole with carbonyl compounds to afford the corresponding bis(indolyl)methanes in good yields in molten tetrabutylammonium bromide as an ionic liquid. Notable features of this new procedure are shorter reaction times, cleaner reaction profiles, and simple experimental and work-up procedures.     

Indium triflate-catalyzed coupling of indoles with acyl phosphonates: synthesis of bis(indolyl)methane phosphonates

The coupling reaction of N-methylindole with alkyl and aryl phosphonate is described. The reaction works in the presence of 10 mol % of indium triflate and furnished bis(indolyl)methane phosphonates in good yield and high selectivity.     

Synthesis,antibacterial and anti-inflammatory activity of bis(indolyl)methanes

A series of bioactive bis(indolyl)methanes are synthesized by one-pot green reaction of indole with various substituted aldehydes by microwave irradiation under solvent free conditions. The antibacterial activity against Staphylococcus aureus and anti-inflammatory activity of the synthesized bis(indolyl)-methanes are evaluated in vitro and compared to standard drugs tetracycline and diclofenac, respectively. The majority of the compounds showed good antibacterial and anti-inflammatory activity. Interestingly, compounds 3j, 3i, 3k and 3g exhibited much higher anti-inflammatory activity than the standard diclofenac drug and thus qualify for clinical trials to be used as an anti-inflammatory compound.     

An efficient and clean synthesis of bis(indolyl)methanes in a protic solvent at room temperature

Electrophilic substitution reactions of indoles with various aldehydes were carried out in a protic solvent at room temperature in the absence of any other catalyst to afford bis(indolyl)-methanes in excellent yields.     

An effective green and ecofriendly catalyst for synthesis of bis(indolyl)methanes as promising antimicrobial agents

An effective and suitable meglumine‐catalyzed high‐yielding process was considered and engaged for the synthesis of new bis(indolyl)methanes at ambient temperature under aqueous conditions. The catalytic reaction proceeds very smoothly. Clean reaction, ease of product isolation/purification, easily available reactant and ecofriendly reaction conditions are the notable advantages of the present methodology. All the title compounds were characterized by IR, 1H, ¹³C NMR, and mass spectra. All the synthesized compounds were tested for antimicrobial activity, and the results indicated that most of the synthesized compounds exhibited excellent activity against the tested microorganisms. In this new series, compound 3l , having nitro substituent on the aromatic ring, showed exceptional potent inhibitory activity against Pseudomonas aeruginosa and Penicillium chrysogenum.     

Synthesis of bis(indolyl)methanes under catalyst-free and solvent-free conditions

Abstract

Condensation of indole with aromatic aldehydes has been carried out without using any catalyst and solvent to give bis(indolyl)methanes.