Three-component Reaction Of Aldehydes Research Articles

Cu (II) Complex Stabilized on Fe3O4@SiO2 Nanoparticles: An Effective and Recoverable Catalyst for the Preparation of Chromene Derivatives

In the present research, we introduce a simple and efficient method for the synthesis of a new heterogeneous nanocatalyst including [Fe3O4@SiO2-L-Cu(II)] via immobilizing Cu (II) on the surfaces of Fe3O4@SiO2 nanoparticles (NPs). The prepared nanocatalyst was characterized by vibration sample magnetometer (VSM), EDS, X-ray diffraction (XRD), TGA, and Field emission scanning microscopy (FE-SEM) spectroscopic methods. The obtained magnetic nanocomposite showed excellent catalytic activity for the preparation of some chromene derivatives via a three-component reaction of aldehydes, 4‐hydroxycoumarin, and 2‐hydroxynaphthalene‐1,4‐dione. This synthetic procedure provides various benefits, including cost-saving, excellent yields in short reaction times (88–98%), low catalyst loading, and catalyst reusability.

Catalyst-Controlled Selectivity Switch in Three-Component Reaction: An NHC-Catalyzed Strategy for the Synthesis of δ-Lactone-Fused Spirobenzofuran-3-ones.

An efficient, three-component reaction of aldehydes and benzofuran-3-ones was developed. This process provides a new approach for the preparation of synthetically and biologically important spirobenzofuran-3-one derivatives with moderate-to-good yields under mild conditions. A switch of intramolecular to intermolecular domino Michael–aldol–lactonization leading to differential product formation was achieved by different NHCs catalysis.

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%).

Application of polyionic magnetic nanoparticles as a catalyst for the synthesis of carbonitriles with both indole and triazole moieties via a cooperative geminal-vinylogous anomeric-based oxidation.

Three-component reaction of aldehydes with 3-(1H-indol-3-yl)-3-oxopropanenitrile and 1H-1,2,4-triazol-5-amine under the solvent-free condition at 70°C was effectively performed in the presence of 2mg of polyionic magnetic nanoparticles with pyrazine bridge [Fe3O4@SiO2@(CH2)3]2-Pyrazinium-[TCM]2 as a catalyst for the synthesis of 7-aryl-5-(1H-indol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles via a cooperative anomeric-based oxidation. The polyionic magnetic nanoparticles catalyst was simply recovered and reused four successive runs. The morphology and structure of MNPs catalyst were investigated by numerous techniques such as XRD, FT-IR, EDX, WDX, FE-SEM, TEM, TGA, DTA, and VSM. The obtained products are reported for the first time that were identified by various analyses techniques such as melting point, FT-IR, 1H NMR, 13C NMR, and elemental analysis (CHN). A term entitled a cooperative geminal-vinylogous anomeric-based oxidation was introduced for the latter step of the reaction mechanism for the first time. Synthesis of 7-aryl-5-(1H-indol-3-yl)-[1,2,4]triazolo[1,5-a]pyrimidine-6-carbonitriles by using [Fe3O4@SiO2@(CH2)3]2-Pyrazinium-[TCM]2 MNPs as a catalyst.

Heterogeneous gold(I)-catalyzed three-component reaction of aldehydes, alkynes, and orthoformates toward propargyl ethers

A novel and efficient heterogeneous gold(I)-catalyzed three-component reaction of aldehydes, alkynes, and orthoformates has been developed that proceeds smoothly in dichloroethane (DCE) at 83 °C in the presence of 5 mol% magnetic nanoparticles-anchored phosphine gold(I) complex (Fe3O4@SiO2-P-AuOTf) and offers a general and practical approach for the preparation of a variety of propargyl ethers with good yields. This heterogeneous gold(I) catalyst can be facilely recovered by simply applying an external magnetic field and recycled at least eight times without any apparent decrease in the catalytic efficiency.

Hantzsch-Like Three-Component Synthesis of 9,10-Dihydro-3H-10a-azaphenanthrene-2,4-dicarbonitriles

A novel series of 9,10-dihydro-3H-10a-azaphenanthrene-2,4-dicarbonitrile derivatives that contain a bridgehead nitrogen were prepared by a three-component reaction of aldehydes, 2-(6,7-dimethoxy-3,4-dihydroisoquinolin-1-yl)acetonitrile, and 3-aminocrotononitrile in acetic acid.

An Efficient, Potassium Carbonate-Catalysed, Three-Component Reaction of Aldehydes, Malononitrile and Amidines Leading to Highly Functionalized Pyrimidines in Aqueous Media

Various 4-amino-5-cyanopyrimidines were readily prepared in a few minutes with good yields through a one-pot, three-component reaction of aldehydes, malononitrile and amidines in aqueous media in the presence of catalytic amounts of potassium carbonate. Short reaction times, high efficiency, generality of the method, synthesis of new derivatives, inexpensiveness, and non-toxicity of the catalyst/solvent are the interesting features of this method, which make it eco-friendly and highly attractive.

Hantzsch-Like One-Pot Three-Component Synthesis of Heptaazadicyclopenta[a,j]anthracenes: A New Ring System

A concise and efficient approach to novel tetrahydroheptaazadicyclopenta[a,j]anthracene-5,7-diones, by the reaction of aldehydes with two moles of 7-amino-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-5-one is reported. Also, pyrazolo[1,5-a]pyrido[3,2-e]pyrimidine-7-carbonitrile derivatives were prepared by a three-component reaction of aldehydes, 7-amino-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-5-one, and 3-aminocrotononitrile.

Hantzsch-Like One-Pot Three-Component Synthesis of Heptaazadicyclopenta[a,j]anthracenes: A New Ring System

A concise and efficient approach to novel tetrahydroheptaazadicyclopenta[a,j]anthracene-5,7-diones, by the reaction of aldehydes with two moles of 7-amino-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-5-one is reported. Also, pyrazolo[1,5-a]pyrido[3,2-e]pyrimidine-7-carbonitrile derivatives were prepared by a three-component reaction of aldehydes, 7-amino-2-methyl-3-phenylpyrazolo[1,5-a]pyrimidin-5-one, and 3-aminocrotononitrile.

An efficient, multicomponent, green protocol to access 4, 7-dihydrotetrazolo [1, 5-a] pyrimidines and 5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-ones using PEG-400 under microwave irradiation

A facile one-pot synthesis of ethyl 5-methyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine, 5-tert-butyl-4,7-dihydrotetrazolo[1,5-a]pyrimidine, 6,6-dimethyl-5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one and 5,6,7,9-tetrahydrotetrazolo[5,1-b]quinazolin-8(4H)-one derivatives were described via a three-component reaction of aldehyde, 5-aminotetrazole and diketones in PEG-400 under microwave irradiation at 110 °C for 30 min. A wide range of diketones such as ethylacetoacetate, tert-butyl acetoacetate, 5,5-dimethylcyclohexane-1,3-dione and 1,3-cyclohexanedione were utilized to carry out the synthesis of different dihydrotetrazolo[1,5-a]pyrimidines and tetrahydrotetrazolo[1,5-a]quinazolinones. This method has the advantage of green protocol, operational simplicity, high yields, recyclability of the solvent and involves isolation of the final product without column purification. The scope of this reaction tolerates with aromatic, heteroaromatic and alicyclic aldehydes.

Visible-Light-Initiated One-Pot, Three-Component Synthesis of 2-Amino-4H-pyran-3,5-dicarbonitrile Derivatives.

A novel approach for the visible-light-initiated synthesis of 2-amino-4H-pyran-3,5-dicarbonitrile derivatives via a one-pot, three-component reaction of aldehydes or isatins, malononitrile, and α-cyano ketones has been developed. The reaction was carried out at room temperature in ethanol/water to give the corresponding products with a wide range of functional groups in high yields. This process did not require any additives or chromatographic separation and could be applied for gram-scale synthesis.

Synthesis of novel multi-OH functionalized ionic liquid and its application as dual catalyst-solvent for the one-pot synthesis 4H-pyrans

In the present work, triethanolammonium 3-hydroxypropane-1-sulfonate [TEA][HPS] as a novel multi-OH functionalized ionic liquid was synthesized. [TEA][HPS] was characterized by 1HNMR, 13CNMR, FT-IR and elemental analysis. In addition to structural study, some physical properties (such as TGA, solubility, conductivity, pH, density and viscosity) of new ionic liquid were determined. The performance of [TEA][HPS] ionic liquid as catalyst and solvent was investigated for the one-pot synthesis of 4H-pyrans through three-component reaction of aldehyde, malononitrile and alkyl acetoacetate at room temperature. [TEA][HPS] ionic liquid could be easily recycled and reused six times without any appreciable decrease in activity. In this research, six of the 4H-pyran derivatives were produced for the first time and also spectra data of all products was reported. Moreover, the biodegradability potential of the [TEA][HPS] ionic liquid was studied using BOD5 parameter [the difference between initial and final dissolved oxygen (DO) after the incubation of five-day]. The obtained results were specified that biodegradability of new ionic liquid is acceptable.

Chloroamine-T Promoted Three-Component Reaction of Aldehydes, Hydrazines and Fumarate Esters for the Construction of Tetra-substituted Pyrazole Derivatives

Chloroamine-T Promoted Three-Component Reaction of Aldehydes, Hydrazines and Fumarate Esters for the Construction of Tetra-substituted Pyrazole Derivatives

Synthesis of 3,4,5-substituted furan-2(5H)-ones using Al-doped ZnO nanostructure

Al-doped ZnO nanostructures were prepared via a simple precipitation method and were characterized by several techniques including XRD, TEM, EDX, UV–Vis, and DLS. All XRD patterns show the hexagonal single-phase structure of pure and Al-doped ZnO nanopowders without impurity. The samples consist of particles with average sizes ranging from 53 to 60 nm measured by DLS technique. Next, the catalytic activity of pure and Al-doped ZnO nanopowders was investigated in terms of synthesis of 3,4,5-substituted furan-2(5H)-one derivatives using the three-component reaction of aldehydes, aromatic amines, and acetylenic esters. This procedure has advantages such as high yields, simple methodology, and easy work-up.

A molybdenum(VI) Schiff base complex immobilized on functionalized Fe3O4 nanoparticles as a recoverable nanocatalyst for synthesis of 2-amino-4H-benzo[h]chromenes

A dioxomolybdenum(VI) complex of a Schiff base, immobilized on the surface of modified Fe3O4 with a silica coating, has been synthesized and characterized by spectroscopic and microscopic techniques including FTIR, TGA, ICP, SEM, EDX, VSM, and XRD analyses. The catalytic performance of this material has been evaluated for the preparation of 2-amino-4H-benzo[h]chromenes via the one-pot, three-component reaction of aldehydes, malononitrile, and 1-naphthol under solvent-free conditions. The benefits of this protocol are short reaction time, simple workup procedure, and high yields of products. Also, the synthesized nanocatalyst could be separated easily from the reaction mixture using an external magnet and reused for four consecutive times with only minor degradation of its catalytic performance.

Synthesis of pyrimido [4, 5-b] indoles using heteropoly-11-molybdo-1-vanadophosphoric acid supported on montmorillonite K10 clay as catalyst: A Green Approach

A method for synthesis of pyrimido [4, 5-b] indole derivatives has been developed through the one-pot, three-component reaction of aldehyde, oxindole, urea (or) thiourea derivatives in the presence of catalytic amount of Keggin-type heteropoly acid, heteropoly-11-molybdo-1-vanadophosphoric acid, H4[PMo11VO40].32H2O supported on montmorillonite K10 clay for about 10% (PVMo-K10). Solvent-free heterogeneous reaction condition, simple workup procedure, short reaction time, moderately yield and reusability of the catalyst are the advantages of this protocol.

Synthesis and biological activity of new 2,6-diphenyl-4-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridines

An efficient one-pot synthesis of new 2,6-diphenyl-4-(1-phenyl-1H-1,2,3-triazol-4-yl)pyridines is presented. This involves the three-component reaction of aldehydes with ketones and ammonium acetate in the presence of catalytic amount of iodine/AcOH. The newly synthesized compounds were characterized by IR, 1H, 13C NMR spectra, and MS data. The products were screened for antibacterial and antifungal activity. Some of the tested compounds exhibited high activity.

A Practical and Diastereoselective Synthesis of Dihydrofurocoumarin from Pyridinium Ylides in Aqueous Medium

A series of 2,3-dihydrofurocoumarins were prepared via a three-component reaction of aldehyde, pyridinium salt and 4-hydroxycoumarin in aqueous ethanol. This method avoids using excessive pyridine and trimethylamine, and has operational simplicity and avoids tedious column chromatography purification. Both aryl aldehydes and aliphatic aldehydes are applicable to this protocol.

Cu(II)–Hydromagnesite Catalyzed Synthesis of Tetrasubstituted Propargylamines and Pyrrolo[1,2-a]quinolines via KA2, A3 Couplings and Their Decarboxylative Versions

A novel copper supported on hydromagnesite (Cu/HM) nanomaterial was prepared by a simple impregnation method at room temperature and characterized by PXRD, SEM, TEM, EDAX, XPS, ICP-AES and FT-IR techniques. The EDAX and XPS results revealed the presence of 8.82 wt % of copper in (+2) oxidation state. Three-component coupling of ketone and amine with alkyne to afford tetrasubstituted propargylamine is known as KA2 coupling, whereas the three-component reaction of aldehydes and amine with alkyne to give propargylamine is considered as an A3-coupling reaction. The Cu/HM was found to be an efficient heterogeneous catalyst for KA2 coupling reaction under solvent free condition, and A3 coupling strategy to afford the pyrrolo[1,2-a]quinolines in DEG as a green solvent. The high catalytic activity of Cu/HM in the A3 coupling strategy to afford propargylamine intermediate is due to the synergistic effect of both Cu2+ and Mg2+ active sites. The versatility of Cu/HM catalyst was also studied for the decarboxylative ...

ZrOCl2/nano TiO2 as an Efficient Catalyst for the One Pot Synthesis of Naphthopyranopyrimidines Under Solvent-free Conditions.

ZrOCl(2)/nano-TiO(2) has been used as an efficient catalyst for the preparation of naphtho[1',2':5,6]pyrano[2,3-d]pyrimidine derivatives by the three-component reaction of aldehydes, β-naphthol and 1,3-dimethylbarbituric acid. The advantages of the reaction are solvent-free conditions, short reaction times, easy workup, good to excellent yields, and cost-effective and reusable catalyst.