Three-component Reaction In Water Research Articles

Synthesis of 2-Benzyl-3-(2-oxo-2-phenylethyl)isoindolin-1-one Derivatives in Water under Catalyst-Free Conditions

AbstractWe have developed a catalyst-free synthesis of a series of isoindolinone derivatives via a one-pot, three-component reaction in water using o-formylbenzoic acids, primary amines, and acetophenones as starting materials. An investigation of the influence of the solvent, the substrate molar ratio, the temperature, and the reaction time revealed that the reaction proceeded optimally in water at 70 °C over 12 hours to afford a wide range of isoindolinone derivatives in yields of up to 93%. This method has the advantages of mild reaction conditions, environmental friendliness, and a broad substrate scope.

Solvent Selective Polyacrylonitrile Fiber as a Recyclable Catalyst for the Knoevenagel-Michael Reaction in Water

Heterogeneous catalysis is an important branch of sustainable chemistry. In this work, a series of polyacrylonitrile fiber (PANF) fiber catalysts (PANF-E, PANF-EDs, and PANF-D) with different catalytic micro-environments are developed and characterized by elemental analysis, Fourier-transfer infrared spectroscopy, x-ray diffraction, thermogravimetric/differential scanning calorimetry analysis, scanning electron microscopy, and mechanical strength measurements to demonstrate the successful immobilization of the different amines as well as evaluate the physical strength and thermal stability of the fiber catalysts at different stages. The catalytic activities of the fiber catalysts are tested by one-pot three-component Knoevenagel-Michael reaction to the synthesis of substituted 2-amino-4H-chromenes in which the influences of surface polarities, kinds and proportions of functional groups on the fiber catalysts activities were investigated. Among the prepared catalysts, the PANF-D with higher density of tertiary amino group and hydrophilic micro-environment exhibited the best catalytic activity to efficiently catalyze the three-component reaction in water with excellent substrate suitability (92-98%). In addition, the catalyst can be easily separated from the catalytic system and conveniently reused at least ten times. Moreover, the PANF-D performs well in scaled-up experiment in a simple fixed-bed reactor with a yield of 97% which allows it to have great potential for further cleaner industrial applications.

Synthesis of a new series of benzo[d]imidazo[2,1-b]thiazole-1-ium hydroxides by a one-pot, three-component reaction in water

Herein, we report the green synthesis of a new series of benzo[d]imidazo[2,1-b]thiazole-1-ium hydroxide derivatives by a one-pot, three-component reaction of arylglyoxals, quinoline-2,4-diol, and 2-aminobenzothiazole in the presence of TEA/AcOH (1:2) as a catalyst at 50 °C in water, which appears as a green solvent. The structures of all 12 examples were confirmed by 1H NMR, 13C NMR, mass spectral data, and FT-IR. This procedure provides mild reaction conditions, using green solvent, high yields, easy work-up and simple isolation of structurally divers tricyclic benzo[d]imidazo[2,1-b]thiazole derivatives which may have biological and pharmaceutical activities.

A recyclable Amberlyst-15-catalyzed three-component reaction in water to synthesize diarylmethyl sulfones

A recyclable Amberlyst-15-catalyzed three-component reaction in water was developed to synthesize asymmetric diarylmethyl sulfones in good to excellent yields with a wide substrate scope.

Three-Component Reactions in Water with a Supported Cu(I) Acetylacetonate Composite

Key words copper catalysis - multicomponent reaction - ionic liquids - aqueous medium

An efficient synthesis of imidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxides by a one-pot, three-component reaction in water

Abstract An improved synthesis of 2-ethyl-5-(2-hydroxy-4-oxoquinolin-3(4H)-ylidene)-6-aryl-5,6-dihydroimidazo[2,1-b][1,3,4]thiadiazol-7-ium hydroxide derivatives 4a–k via the reaction of aryl glyoxal monohydrates 1a–k, quinoline-2,4-diol 2 and 2-amino-[1,3,4]thiadiazole (3) in the presence of Et3N/sulfamic acid in H2O is described. This green protocol is characterized by the use of the readily available catalyst and reactants, short reaction times, operational simplicity and high yields of products. The structures of all compounds were characterized by 1H NMR, 13C NMR and Fourier-transform infrared (FT-IR) spectral data and microanalyses.

An efficient and green synthesis of ferrocenyl-quinoline conjugates via a TsOH-catalyzed three-component reaction in water.

An efficient and green synthesis of 4-ferrocenylquinoline derivatives through a TsOH-catalyzed three-component reaction of aromatic aldehydes, amines and ferrocenylacetylene in water has been successfully developed. This strategy is a powerful method for the construction of diverse ferrocenyl-quinoline conjugates from simple available starting materials as it minimized the use of metal catalyst and organic solvent in the reaction process. The conjugates feature unique structures and excellent electronic properties. Moreover, a plausible mechanism for this TsOH-catalyzed three-component reaction was proposed and assessed.

Efficient microwave-assisted diastereoselective synthesis of indole-based 4,5-dihydrofurans via a one-pot, three-component reaction in water

The combination of two or more different heterocyclic moieties in a single molecule would enhance biological activity significantly. The indole and furan scaffolds are promising candidates in drug design, and they have been widely found in natural products and therapeutic agents. Owing to their pharmaceutical importance, there is an urgent need to design rapid, efficient and environmentally benign protocols for the synthesis of indole–dihydrofuran biheterocycles. Herein, we have developed a novel ecofriendly approach for the diastereoselective synthesis of indole-based 4,5-dihydrofurans through a three-component reaction of 3-cyanoacetyl indoles with various aldehydes and N-phenacylpyridinium bromides in the presence of potassium carbonate as an inexpensive and non-toxic base in water under low power microwave irradiation. The findings show that aromatic and heteroaromatic aldehydes tolerated well in this reaction. The products were obtained in 85–98% yields in 4–20 min. The advantages of this method consist of the environmental friendly reaction conditions, use of green solvent and safe base, availability of raw materials, wide range of usable substrates, short reaction times, excellent yields and absence of any tedious workup or purification.

Efficient Synthesis of 3-Substituted Indoles via a Base-Free Copper-Catalysed Three-Component Reaction in Water

The preparation of sixteen 3-substituted indoles in good to excellent yields under environmentally friendly conditions has been achieved via a three-component reaction in water of an indole, an aldehyde and malononitrile (or ethyl 2-cyanoacetate) catalysed by 5 mol% of 2-pyrrolecarbaldiminato-Cu(II).

1603899: Efficient synthesis of 3-substituted indoles via a base-free copper-catalysed three-component reaction in water – ESI

1603899: Efficient synthesis of 3-substituted indoles <i>via</i> a base-free copper-catalysed three-component reaction in water – ESI

A novel and green synthesis of indolone-N-amino acid derivatives via the Passerini three-component reactions in water

Abstract A green Passerini three-component reaction of 2-(4-oxo-4,5,6,7-tetrahydro-1 H -indol-1-yl)acetic acid with alkyl or aryl isocyanides and aldehydes was reported under aqueous conditions at 35 °C for 1 h, and 21 indolone- N -amino acid derivatives were prepared in high yields of 42%–99%. Their structures were characterized by IR, ESI–MS, NMR and elemental analysis, and the possible mechanisms have been also proposed. The highly efficient and eco-friendly method provides a facile access to a library of indolone- N -amino acid derivatives for future research on bioactivity screening.

A convenient and mild synthesis of new 2-aryl-3-hydroxy-6,7-dihydro-1H-indol-4(5H)-ones via a one-pot, three-component reaction in water

A simple and convenient synthesis of 2-aryl-3-hydroxy-6,7-dihydro-1H-indol-4(5H)-ones is achieved in high yields via the one-pot, three-component reaction of arylglyoxals, 1,3-cyclohexanedione, and ammonium acetate in water under reflux conditions.

Trifluoroacetic acid catalyzed thiophenylmethylation and thioalkylmethylation of lactams and phenols via domino three-component reaction in water

A new method for thiophenylmethylation and thioalkylmethylation of lactams and phenols has been described.

Ionic liquid catalyzed one-pot synthesis of spiropyran derivatives via three-component reaction in water

Abstract The ionic liquid [H3N+CH2CH2OH][CH3COO-] (HEAA) catalyzes a three-component, one-pot condensation of malononitrile/ethyl cyanoacetate, 1,3-dicarbonyl compound/enol, and quinone or ninhydrin in water to afford a spiropyran derivative. This method has advantages of mild reaction conditions, short reaction time, and environmental friendliness.

Synthesis of Arylmethylidene-isoxazol-5(4H)-ones via Three-Component Reaction in Water Catalyzed by Sodium Tetraborate

A series of arylmethylidene-isoxazol-5(4H)-ones have been prepared via a one-pot, three-component cyclocondensation process between aromatic aldehydes, ethyl acetoacetate, and hydroxylamine hydrochloride in good yields. It was found that sodium tetraborate to be an efficient and reusable catalyst for this condensation reaction under aqueous conditions at room temperature. Mild conditions, green, safe, shorter reaction times, eco-friendly, no use of organic solvent, and easy work-up of the products are remarkable advantages of this process.

A green one-pot synthesis of N-alkyl-2-(2-oxoazepan-1-yl)-2-arylacetamide derivatives via an Ugi four-center, three-component reaction in water

This work describes a green and efficient one-pot synthesis of N-alkyl-2-(2-oxoazepan-1-yl)-2-arylacetamide derivatives via an Ugi four-center, three-component reaction of 6-aminohexanoic acid, aromatic aldehydes, and isocyanide derivatives in water under reflux conditions in the absence of a catalyst.

Multicomponent Reactions Stereo- and Regioselective Three-Component Reaction in Water: Synthesis of Triazole Substituted &amp;#946;-Lactams Via Click Chemistry

Three-component reaction in water was used to prepare a series of triazole substituted trans-β-lactams from the corresponding trans-4-acetoxy-lactam, sodium azide, and alkynes via a Cu(I)-catalyzed click chemistry with base free. This highly stereo- and regioselective procedure is simple, clean and efficient. Keywords: Three-component reaction, β-lactam, 3R,4R-4-acetoxy-3-[(R)-1-((tert-butyldimethyl-silyl)oxy)-ethyl]-2-azetidinone, click reaction, triazole, stereo- and regioselective reaction, monobactams, carbacephems, carbapenems, sulfinylazetidin

Synthesis of 3-indole derivatives by copper sulfonato Salen catalyzed three-component reactions in water

An efficient three-component reaction of indole, aldehyde, and malononitrile in water catalyzed by a copper(II) sulfonato Salen complex afforded 3-indole derivatives in good to excellent yields up to 97%.

Synthesis of fluorescent hydroxyl naphthalene-1,4-dione derivatives by a three-component reaction in water

An efficient one-pot synthesis of fluorescent hydroxyl naphthalene-1,4-dione derivatives by a simple, atom-economical and three-component reaction of 2- hydroxynaphthalene-1,4-dione, aromatic aldehydes and heterocyclic or carbocyclic amines in the presence of a catalytic amount of InCl 3 in refluxing water is reported. The structures of the compounds were confirmed by IR, 1H NMR, 13C NMR, and elemental analysis. UV- visible absorption coefficient, maximum wavelength and fluorescence emission wavelength were measured in methanol. The products were fluorescent in solution emitting at green light (546–560 nm). The advantages of this procedure are mild reaction conditions, high yields of products, operational simplicity and easy work-up procedures. The workup of these very clean reactions involves only a filtration and simple washing step with EtOH.

A simple and effective approach to the synthesis of rhodanine derivatives via three-component reactions in water

A facile and direct synthetic entry to rhodanine derivatives via the three-component coupling of carbon disulfide, primary amines, and acetylenic esters under neutral conditions in water is reported.