One-pot Three-component Reaction Of Aldehydes Research Articles

A Green and Ecofriendly Catalytic System for One-Pot Three-Component Synthesis of 5-Substituted 1H-Tetrazoles Under Microwave Irradiation

In this research work, the high-yielding and simple synthesis of 5-substituted 1H-tetrazoles derivatives through the one-pot three-component reaction of aldehydes, hydroxylamine hydrochloride and sodium azide catalyzed by MNPs-Picolylamine-Cu(OAc)2 nanocomposite in water under microwave irradiation has been reported. The MNPs-Picolylamine-Cu(OAc)2 nanocomposite is successfully fabricated through the immobilization of copper (II) acetate stabilized on magnetic Fe3O4 nanoparticles modified with Picolylamine [MNPs-Picolylamine-Cu(OAc)2] and then is well analyzed by various techniques such as FT-IR, XRD, TGA, SEM, TEM, EDS, VSM and ICP-OES. At the end of the reaction, the MNPs-Picolylamine-Cu(OAc)2 catalyst can be easily recycled and reused and the products obtained had high efficiency and purity.

An Efficient One-pot Stereoselective Synthesis of 2,6-disubstituted 4-thiocyanatotetrahydropyrans

An efficient stereoselective synthesis of 2,6-disubstituted-4-thiocyanatotetrahydropyrans has been developed through a one-pot three-component reaction of aldehydes, trimethyl allylsilane, and NH<sub>4</sub>SCN in the presence of BF<sub>3</sub>.Et<sub>2</sub>O at room temperature. The products are formed rapidly (10-30 min) in excellent yields (78-98%).

One-pot three-component synthesis of α-aminonitriles using sodium dihydrogen phosphate as a catalyst at room temperature

Sodium dihydrogen phosphate was applied as an efficient and inexpensive catalyst for the synthesis of biologically potent α-aminonitrile derivatives through a one-pot three-component reaction of aldehyde, amine and trimethylsilyl cyanide. The reactions were easily carried out under mild, green and eco-friendly conditions in ethanol at room temperature affording high yields of the products in short times.

Efficient Rapid Access to Biginelli for the Multicomponent Synthesis of 1,2,3,4-Tetrahydropyrimidines in Room-Temperature Diisopropyl Ethyl Ammonium Acetate.

The diisopropyl ethyl ammonium acetate (DIPEAc)-promoted Biginelli protocol has been developed for the first time by a successive one-pot three-component reaction of aldehydes, ethylcyanoacetate/ethyl acetoacetate, and thiourea/urea to afford pharmacologically promising 1,2,3,4-tetrahydropyrimidines in high yields at room temperature. The key benefits of the present scheme are the capability to allow a variability of functional groups, short reaction times, easy workup, high yields, recyclability of the catalyst, and solvent-free conditions, thus providing economic and environmental advantages. In addition, a series of 4-oxo-6-aryl-2-thioxo-1,2,3,4-tetrahydropyrimidine-5-carbonitriles analogues were synthesized and selected for their in vitro antifungal and antibacterial activities.

A novel catalytic one-pot three-component reaction of aldehydes, o-phenylenediamine derivatives and isocyanides for synthesis of 3,4-dihydroquinoxalin-2-amine derivatives in the presence of zirconium tetrachloride

A simple and efficient one-pot procedure for the synthesis of biologically interesting 3,4-dihydroquinoxalin-2-amine derivatives through a three-component condensation reaction of o-phenylenediamines, carbonyl compounds and isocyanides in ethanol at room temperature is described. In this work, unlike the other methods, aldehydes reacted as well as ketones in the presence of 10 mol% of zirconium tetrachloride as catalyst to afford good to excellent yields of products. This methodology is of great value because of its environmentally benign character, high yields, ease of handling and reliable for both aldehydes and ketones. The newly synthesized compounds were systematically characterized by IR, 1H NMR, 13C NMR and elemental analysis. A novel catalytic one-pot three-component reaction of aldehydes, o-phenylenediamine derivatives and isocyanides for synthesis of 3,4-dihydroquinoxalin-2-amine derivatives in the presence of zirconium tetrachloride .

4-(4′-Diamino-di-phenyl)-sulfone supported on hollow magnetic mesoporous Fe3O4@SiO2 NPs: As a reusable and efficient catalyst for the synthesis of ethyl 2-amino-5,10-dihydro-5,10-dioxo-4-phenyl-4H benzo[g]chromene-3-carboxylates

4-(4′-diamino-di-phenyl)-sulfone supported on hollow magnetic mesoporous (HMMS) Fe3O4@SiO2 NPs has been used as a novel and efficient catalyst in the preparation of ethyl 2-amino-5,10-dihydro-5,10-dioxo-4-phenyl-4H benzo[g]chromene-3-carboxylates by a simple one-pot three-component reaction of aldehydes, ethyl cyanoacetate and 2-hydroxynaphthalene-1,4-dione under reflux conditions in ethanol. Wide range of products, excellent yields in short times, reusability of the catalyst, low catalyst loading and environmental benignity are some of the important features of this protocol.

A magnetic metal–organic framework as a highly active heterogeneous catalyst for one-pot synthesis of 2-substituted alkyl and aryl(indolyl)kojic acid derivatives

A novel magnetic metal–organic framework, NiFe2O4@MOF-5, was prepared and demonstrated to be a highly efficient catalyst for the one-pot three-component reaction of aldehyde, indole, and kojic acid.

Facile and rapid synthesis of divers xanthene derivatives using lanthanum(III) chloride/chloroacetic acid as an efficient and reusable catalytic system under solvent-free conditions

LaCl3/ClCH2COOH was used as an efficient, and recyclable catalytic system for synthesis of 11H-benzo[a]xanthene-11-one, hexahydro-1H-xanthene- 1,8(2H)-dione and 11-aryl-10H-diindeno[1,2-b:2?,1?-e]pyran-10,12(11H)-dione derivatives via a one-pot three-component reaction of aldehydes, 2-naphthol, and cyclic 1,3-dicarbonyl compounds. The reactions proceeded rapidly at 70?C under solvent-free conditions and the desired products were obtained in good to excellent yields.

Highly efficient synthesis of α-aminophosphonates catalyzed by hafnium(IV) chloride

A highly efficient one-pot method for the synthesis of a variety of α-aminophosphonates via the one-pot three-component reaction of aldehyde, amine, and phosphite has been developed using only 2mol% HfCl4 as the catalyst. The NMR evidence strongly indicated the catalytic roles of Hf(IV) on the activation of aldehyde, phosphite, and imine intermediate.

Efficient synthesis of novel imidazo[1,2-a]pyrimidine derivatives via one-pot three-component procedure

Synthesis of novel derivatives of imidazo[1,2-a]pyrimidine from one-pot three-component reaction of aldehydes, 2-amino-benzimidazole, and α-tetralone in the presence of catalytic amount of p-toluene sulfonic acid under reflux condition in EtOH has been presented. The simplicity and safety of the process, high yields and short reaction times were the main advantages of this protocol.

Synthesis and evaluation of antimicrobial activity of 2-aminobenzothiazolomethyl naphthol derivatives

An efficient method is described for the synthesis of 2-aminobenzothiazolomethyl naphthol derivatives by one-pot three-component reaction of aldehydes, 2-naphthol, and 2-amino benzothiazole using triton X-100 as a catalyst in water with good yield. The synthesized compounds have been characterized by IR, 1H NMR, 13C NMR, and mass spectra. The synthesized compounds were screened for their antibacterial activity against gram-positive and gram-negative bacteria viz. Staphylococcus aureus, Pseudomonas aeruginosa, Salmonella typhi, Escherichia coli, Bacillus cereus, and Providencia rettegeri and fungal activity against fungal strain such as Aspergillus niger, Aspergillus fumigatus, and Aspergillus flavus. Synthesized compounds exhibited MICs value between 3.25 and 12.5 μg/mL against bacterial strains and 6.25 and 12.5 μg/mL against fungal strains as shown in Tables 4 and 5, respectively. Derivatives 5c and 5h were equipotent activity as ciprofloxacin against E. coli and 5k against P. aeruginosa and B. cereus. Derivatives 5e, 5g, and 5k exhibited excellent antifungal activity against all tested fungal strains. Ciprofloxacin and fluconazole have been used as standard drugs for antibacterial and antifungal activity, respectively.

Silver iodide nanoparticle as an efficient and reusable catalyst for the one-pot synthesis of benzofurans under aqueous conditions

Recyclable heterogeneous AgI nanoparticles were efficiently catalysed one-pot three-component reaction of aldehydes, secondary amines and alkyne in aqueous media. This method provides a novel and improved approach for the synthesis of 2,3-disubstituted benzo[b]furan derivatives to obtain excellent yields, short reaction times and low catalyst loading. An efficient and environmentally friendly method for the one-pot synthesis of 2,3-disubstituted benzo[b]furans is described through three-component reaction of aldehydes, secondary amines and alkyne using AgI nanoparticles in aqueous media. The present approach provides several advantages including high yields, short reaction times, reusability and low catalyst loading.

ChemInform Abstract: P‐Dodecylbenzenesulfonic Acid: A Highly Efficient Catalyst for One‐Pot Synthesis of α‐Aminophosphonates in Aqueous Media.

A highly efficient one-pot three-component reaction of aldehydes or ketones, amines, and trimethyl or triethyl phosphite catalyzed by p-dodecylbenzensulfonic acid is developed for the synthesis of α-aminophosphonates at room temperature in water. © 2013 Wiley Periodicals, Inc. Heteroatom Chem 24:174–178, 2013; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.21079

T3P®-promoted Kabachnik–Fields reaction: an efficient synthesis of α-aminophosphonates

Abstract A simple and efficient synthesis of α-aminophosphonates has been developed via the one-pot three-component reactions of aldehydes, amines, and trialkyl phosphites. The reactions occurred rapidly at room temperature in the presence of 1 equiv of propylphosphonic anhydride (T3P®) as the condensing agent, and the α-aminophosphonate products were obtained in high yields.

Nano n-propylsulfonated magnetic γ-Fe2O3 as an efficient and reusable catalyst for the synthesis of thioamides

One-pot three-component reactions of aldehydes, amines, and sulfur are carried out in the presence of nano n-propylsulfonated magnetic γ-Fe2O3 as a catalyst for the synthesis of biologically interesting thioamide derivatives. The value of this catalytic method lies in its mild reaction catalyst and conditions, good yields, and ease of handling.

Synthesis of 3,4-Dihydropyrimidin-2(1H)-Ones and Their Corresponding 2(1H)Thiones Using Trichloroacetic Acid as a Catalyst under Solvent-Free Conditions

Trichloroacetic acid was found to be a convenient catalyst for the synthesis of 3,4-dihydropyrimidin-2-(1H)-ones and their corresponding 2(1H)-thiones through a one-pot three-component reaction of aldehydes, alkyl acetoacetate, and urea or thiourea at 70°C under solvent-free conditions.

ChemInform Abstract: Palladium‐Assisted Multicomponent Cyclization of Aromatic Aldehydes, Arylamines and Terminal Olefins under Molecular Oxygen: An Assembly of 1,4‐Dihydropyridines.

The palladium-assisted one-pot three-component reactions of aldehydes, amines and olefins proceeded smoothly to give 2,6-unsubstituted 1,4-dihydropyridines (1,4-DHPs) using molecular oxygen as a sole oxidant. It also provides efficient Pd-catalyzed aerobic oxidation access to the anti-Markovnikov oxidative amination products of olefins from primary aromatic amines and alkenes. The method is atom-efficient, using cheap and easily available starting materials and an environmentally benign oxidant.

Palladium-assisted multicomponent cyclization of aromatic aldehydes, arylamines and terminal olefins under molecular oxygen: an assembly of 1,4-dihydropyridines

The palladium-assisted one-pot three-component reactions of aldehydes, amines and olefins proceeded smoothly to give 2,6-unsubstituted 1,4-dihydropyridines (1,4-DHPs) using molecular oxygen as a sole oxidant. It also provides efficient Pd-catalyzed aerobic oxidation access to the anti-Markovnikov oxidative amination products of olefins from primary aromatic amines and alkenes. The method is atom-efficient, using cheap and easily available starting materials and an environmentally benign oxidant.

A facile and efficient method for synthesis of xanthone derivatives catalyzed by HBF4/SiO2 under solvent-free conditions

HBF4/SiO2 was used as an efficient, green, and inexpensive catalytic system for synthesis of 12-aryl or 12-alkyl-8,9,10,12-tetrahydro-11H-benzo[a]xanthen-11-one derivatives via a one-pot three-component reaction of aldehydes, 2-naphthol, and cyclic 1,3-dicarbonyl compounds. The reactions proceeded rapidly at 80 °C under solvent-free conditions and the desired products were obtained in good to excellent yields.

A convenient one-pot synthesis of 2-(trifluoromethyl)-3,4,7,8-tetrahydro-2 H-chromen-5(6 H)-one derivatives and their further transformations

The trifluoromethyl containing heterocycles, 2-hydroxy-4-aryl-3-(thien-2-oyl)-2-(trifluoromethyl)-3,4,7,8-tetrahydro-2 H-chromen-5(6 H)-one derivatives 4, were synthesized via a one-pot three-component reaction of aldehyde 1 with 1,3-cyclohexanedione 2 and 4,4,4-trifluoro-1-(thien-2-yl)butane-1,3-dione 3 in the presence of a catalytic amount of Et 3N. The effect of bases and solvents on the reaction efficiency and yield was briefly investigated. Treatment of 4 with an excess amount of NH 4OAc in ethanol afforded 2-trifluoromethyl-1 H-quinolin-5-one derivatives 5. Refluxing of 4 with TsOH in CHCl 3 gave the corresponding dehydrated products 8.