Three-component Reaction Of Aryl Aldehydes Research Articles

Silica-Supported Molybdic Acid-Catalyzed Synthesis of New and Known Chromeno-Pyrano[2,3-b]Quinolines through a Green Route

A capable manner for the preparation of chromeno-pyrano[2,3-b]quinoline compounds is outlined. Pyrano[3,2-c]chromene-3-carbonitriles are synthesized via the one pot three-component reaction of aryl aldehydes, malononitrile and 4-hydroxycoumarin in the presence of silica sodium carbonate (SSC) as a heterogeneous basic catalyst. Next, the prepared pyrano[3,2-c]chromene-3-carbonitrile is reacted with cyclohexanone by using silica-supported molybdic acid (SSMA) as a worthy and recyclable catalyst for producing recognized and unrecognized chromeno-pyrano[2,3-b]quinoline derivatives under solvent-free conditions in good to excellent yields.

Molybdic Acid-Functionalized Nano-Fe3O4@TiO2 as a Novel and Magnetically Separable Catalyst for the Synthesis of Coumarin-Containing Sulfonamide Derivatives

Supported molybdic acid on nano-Fe3O4@TiO2 (Fe3O4@TiO2@(CH2)3OMoO3H) has been successfully prepared, char-acterized and applied as a catalyst for the synthesis of sulfonamide containing coumarin moieties. The prepared Fe3O4nanoparticles by coprecipitation of Fe2+ and Fe3+ ions were treated with tetraethyl orthotitanate to obtain Fe3O4@TiO2. By anchoring 3-chloropropyltriethoxysilan on Fe3O4@TiO2 followed by reacting with molybdic acid, the desired catalyst was produced. The synthesized catalyst was characterized using XRD, SEM, EDS, FT-IR and VSM analysis. Fe3O4@TiO2@(CH2)3OMoO3H was used as a catalyst for the synthesis of sulfonamide containing coumarin moieties via a three-com-ponent reaction of aryl aldehydes, para-toluenesulfonamide and 4-hydroxycoumarin or 5,7-dihydroxy-4-methylcou-marin. The catalyst recovery test showed the catalyst is highly reusable without losing its activity.

One-pot synthesis of 1,3,5-triazine-2,4-dithione derivatives via three-component reactions.

A catalyst-free one-pot synthetic methodology was developed for the preparation of 1,3,5-triazine-2,4-dithione derivatives through three-component reactions of arylaldehydes, thiourea, and orthoformates. The procedure tolerated a diverse range of arylaldehydes and orthoformates and provided a rapid entry to a variety of 4-aryl-6-(alkylthio)-3,4-dihydro-1,3,5-triazine-2(1H)-thiones (29 examples). The synthetic strategy relies on the dual role of thiourea in the cyclization with the aldehydes and the alkylation via an intermediate imidate formation. The structures of 1,3,5-triazine-2,4-dithione derivatives were characterized by spectroscopic techniques as well as by single crystal X-ray diffraction.

Divergent synthesis of 1,3,5-tri and 1,3-disubstituted pyrazoles under transition metal-free conditions.

Pyrazole cores are common structural motifs existing in various agrochemicals and pharmaceuticals. Herein, a transition metal-free, three-component reaction of arylaldehydes, ethyl acrylate and N-tosylhydrazones is described, which leads to the formation of 1,3,5-trisubstituted and 1,3-disubstituted pyrazoles divergently under slightly different conditions.

Synthesis, characterization, anti-proliferative properties and DNA binding of benzochromene derivatives: Increased Bax/Bcl-2 ratio and caspase-dependent apoptosis in colorectal cancer cell line

3-Amino-1-aryl-1H-benzo[f]chromene-2-carbonitrile derivatives were synthesized from three-component reaction of arylaldehyde, malononitrile and 2-naphthol in the presence of 1, 4-bis(4-ferrocenylbutyl)piperazine as a new catalyst. Cytotoxic potencies of the compounds were tested on HT-29 cells. 3-Amino-1-(4-fluorophenyl)-1H-benzo[f]chromene-2-carbonitrile (4c) was more active among these compounds and was selected for further studies. Apoptosis was investigated by acridine orange/ethidium bromide (AO/EtBr) double staining and flow cytometry. The qRT-PCR was used to analyze the expression of pro- and anti-apoptotic genes. The binding attributes of 4c with calf thymus DNA (ctDNA) was examined using multi-spectroscopic measurements. We found that 4c had potent cytotoxic activity against HT-29 cells with an IC50 value of 60 µM through induction of cell cycle arrest in the sub-G1 phase and apoptosis. RT-PCR analysis demonstrated down-regulation of Bcl-2 expression, while the expression of Bax, caspase-3, -8 and -9 genes was up-regulated in HT-29 cells incubated with 4c compared with control cells. These studies revealed that 4c interacts with DNA through groove binding mode with the intrinsic binding constant (Kb) of 3 × 102 M−1. Thus, 4c is a valuable candidate for further evaluation as a new series of potent chemotherapeutic family in colon cancer treatment.

A three component one-pot synthesis of N-amino-2-pyridone derivatives catalyzed by KF-Al2O3

Synthesis of 1,6-diamino-4-phenyl-3,5-dicyano-2-pyridone derivatives via a one-pot, three-component reaction of aryl aldehydes, malononitrile, and cyanoacetic hydrazide at room temperature using KF-Al2O3 as a recyclable catalyst have been developed. The reaction proceeds through the initial Knoevenagel condensation between aldehyde and malononitrile in the presence of KF-Al2O3 to form the benzylidene derivative which then undergoes Michael addition with cyanoacetic hydrazide followed by intramolecular cyclization of the resulting intermediate to produce the N-amino-2-pyridones in good to excellent yields. The structure of the synthesized compounds were characterized and established on the basis of their spectral data analysis and single-crystal XRD analysis.

Novel Multicomponent Synthesis of Pyridine-Pyrimidines and Their Bis-Derivatives Catalyzed by Triazine Diphosphonium Hydrogen Sulfate Ionic Liquid Supported on Functionalized Nanosilica.

In this Research Article, we report an efficient synthesis of 1,3-dimethyl-5-aryl-7-(pyridine-3(2)(4)-yl)pyrimidine-2,4(1H,3H)-diones via a three-component reaction of aryl aldehydes, 1,3-dimethyl-6-aminouracil and carbonitriles in the presences of triazine diphosphonium hydrogen sulfate ionic liquid supported on functionalized nanosilica (APTADPHS-nSiO2) as a reusable catalyst under microwave irradiation and solvent-free conditions. The bis-derivatives of pyridine-pyrimidines were also efficiently prepared from dialdehydes and dinitriles. In addition, 3-methyl-1H-pyrazole-5-amine was used successfully instead of 1,3-dimethyl-6-aminouracil under the same conditions to afford the corresponding products in high yields. The catalyst can be reused at least five times without any significant loss of its activity. The easy recovery, reusability and excellent activity of the catalyst as well as easy workup are other noteworthy advantages of this method.

An efficient one-pot synthesis of highly functionalized benzylpyrazolyl pyrido[1,2-a]pyrimidine derivatives using CuFe2O4 nanoparticles under solvent-free conditions

An efficient and green protocol for the synthesis of novel benzylpyrazolyl pyrido[1,2-a]pyrimidine derivatives via three-component reaction of aryl aldehydes, 2-hydroxy-4H-pyrido[1,2-a]pyrimidine-4-ones, and 3-methyl-1-phenyl-1H-pyrazol-5-one has been reported using a magnetically separable and reusable heterogeneous copper ferrite (CuFe2O4) nano-catalyst under solvent-free conditions. CuFe2O4 nanoparticles were characterized by FT-IR, powder X-ray diffraction and transmission electron microscopy. An efficient one-pot synthesis of highly functionalized benzylpyrazolyl pyrido[1,2-a]pyrimidine derivatives using CuFe2O4 nanoparticles under solvent-free conditions.

Microwave-assisted clean synthesis of xanthenes and chromenes in [bmim][PF6] and their antioxidant studies

An efficient one-pot synthesis of xanthene and chromene derivatives by three-component reactions of aryl aldehydes, cyclic 1,3-diketones, and 2-naphthol/4-hydroxy coumarin catalyzed by ionic liquid (IL) [bmim][PF6] under microwave irradiation is described. The present scheme provides several advantages such as short reaction time, mild reaction conditions, good yields, convenient operation, and reuse of IL. In vitro antioxidant activity was evaluated for the synthesized compounds by DPPH method. Compounds 6a, 6h, 6c, 6b, 4k, and 4a showed the highest antioxidant potency.

Phthalimide-N-sulfonic acid: a new and efficient organocatalyst for the Biginelli reaction under solvent-free conditions

Phthalimide-N-sulfonic acid (PISA) was straightforwardly synthesized via addition of chlorosulfonic acid to a solution of potassium phthalimide in dry dichloromethane. This reagent is found to be an efficient solid acidic catalyst in the Biginelli reaction. The three-component reaction of aryl aldehydes, urea/thiourea, and ethyl acetoacetate or acetylacetone occurs by means of 10 mol % of PISA in solvent-free reaction conditions (SFRCs) at 120 °C. The present methodology is a green approach to access a series of 3,4-dihydropyrimidin-2(1H)-ones/thiones in high yields. In addition, the use of PISA as the catalyst offers several notable features such as simple operational procedure, no use of hazardous organic solvents, and recyclability of catalyst.

One-pot multi-component synthesis of pyrimido[4,5-b]indoles in solvent-free condition

Pyrimido[4,5-b]indole derivatives 4 were synthesized from a one-pot three-component reaction of aryl aldehyde 1, oxindole 2 and urea/thiourea 3 in solvent-free condition using ytterbium(III) triflate as catalyst. .

Boric acid-catalyzed multi-component reaction for efficient synthesis of 4H-isoxazol-5-ones in aqueous medium

The one-pot three-component reaction of aryl aldehydes with hydroxylamine hydrochloride and ethyl 3-oxobutanoate/ethyl 4-chloro-3-oxobutanoate/ethyl 3-oxo-3-phenylpropanoate in the presence of boric acid, H3BO3, in water leads to 4H-isoxazol-5(4H)-ones in high yields. The merits of this method are efficiency, simplicity, clean, green, easy work-up, high yields, and shorter reaction times.

ChemInform Abstract: Acetylide Ion(C22‐) as a Synthon to Link Electrophiles and Nucleophiles: A Simple Method for Enaminone Synthesis.

AbstractThe three‐component reaction of aryl aldehyde, calcium carbide and a bulky secondary amine provides a direct synthesis of enaminones (IV).

Tetrakis(acetonitrile)copper(I) Hexafluorophosphate as an Efficient Catalyst for the Synthesis of Triazolo[1,2-a]indazole-1,3,8-trione and 2Hindazolo[2,1-b]phthalazine-trione Derivatives

Tetrakis(acetonitrile)copper(I) hexafluorophosphate, [Cu(CH3CN)4]PF6, was explored as an efficient catalyst to promote the three-component reaction of aryl aldehydes, dimedone and urazole or phthalhydrazide to afford the corresponding triazolo[1,2-a]indazole-1,3,8-trione and 2H-indazolo[2,1-b]phthalazine-trione derivatives respectively in high yields. The reactions were conducted at 80-100 °C under solvent-free conditions. The catalyst was easily prepared from available and inexpensive materials and was quantitatively recovered from the reaction by simple filtration and reused for a number of cycles with almost consistent activity Keywords: 2H-Indazolo[2, 1-b]phthalazine-trione, dimedone, phthalhydrazide, tetrakis(acetonitrile)copper(I)hexafluorophosphate, triazolo[1, 2-a]indazole-1, 3, 8-trione, urazole, phthalazine, pyrazoles, multi-component, vasorelaxant

A mild and highly efficient one-pot three-component reaction for carbon–sulfur bond formation catalyzed by potassium tert-butoxide

Abstract Potassium tert-butoxide has been found to be a highly efficient catalyst for one-pot, three-component reaction of aryl aldehydes, acetophenones, and thiols via Claisen–Schmidt/Michael addition reactions for the synthesis of thia-Michael adducts in high yields. The reactions are best carried out in tert-butyl alcohol at room temperature.

Multicomponent synthesis of 3,5-diaryl-2,6-dicyanoanilines under thermal solvent-free conditions

A facile parallel synthesis of 3,5-diaryl-2,6- dicyanoanilines via three-component reaction of aryl aldehydes, acetophenone derivatives, and malononitrile under thermal green solvent-free conditions in the presence of potassium carbonate and also potassium bicarbonate without using any hazardous materials is described.

Iodine-Catalyzed Synthesis of 12-Aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one Derivatives via Multicomponent Reaction

Iodine efficiently catalyzes the one-pot, three-component reaction of aryl aldehyde, 2-naphthol, and cyclic 1,3-dicarbonyl compound under solvent-free conventional heating conditions to afford the corresponding 12-aryl-8,9,10,12-tetrahydro-benzo[a]xanthen-11-one derivatives. The present approach offers several advantages such as shorter reaction times, good yields, low cost, and mild reaction conditions.

Iodine-Catalyzed Synthesis of 3-Arylbenzoquinoline Derivatives by Three-Component Reactions

A mild, efficient, and general method for the synthesis of benzo[f]quinoline derivatives via three-component reaction of arylaldehyde, naphthalen-2-amine, and acetone or acetophenone is described using iodine as catalyst. The features of this procedure are mild reaction conditions, high yields, and operational simplicity.

An Efficient and Highly Selective Method for the Synthesis of 3-Arylbenzo­quinoline Derivatives Catalyzed by Iodine via Three-Component Reactions

A mild, efficient and highly selective method for the synthesis of benzo[ F]quinoline derivatives via three-component reactions of arylaldehydes, naphthalen-2-amine and ketones or β-keto esters using iodine as catalyst is described. It should be noted that only one product was obtained, with high selectivity, when ketones or β-keto esters with two different α-hydrogen atoms were chosen as reactants.