One-pot Condensation Of Aldehydes Research Articles

Synthesis, computational studies, and Hirshfeld surface analysis of 2H-chromen-2-one and imine derivatives

Some 2H-chromen-2-one and imine derivatives have been synthesized through a one-pot condensation of aldehydes, diethyl malonate, and amine compounds. The compounds obtained have been characterized using FTIR, NMR, GC-MS, and elemental analysis. The single-crystal X-ray structure of 3-[piperidine-1-carbonyl]-2H-chromen-2-one (2) has been presented. Compound 2, recrystallized in the monoclinic space C2/c (no. 15), a = 16.654(15) Å, b = 8.789(7) Å, c = 18.460(18) Å, β = 102.89(5)°, V = 2634(4) Å3, Z = 8, T = 296(2) K, μ(MoKα) = 0.091 mm-1, Dcalc = 1.298 g/cm3, 17626 reflections measured (4.528° ≤ 2Θ ≤ 57.446°), 3321 unique (Rint = 0.0313, Rsigma = 0.0257) which were used in all calculations. The final R1 was 0.0441 (I > 2σ(I)) and wR2 was 0.1329 (all data). The experimental bond lengths, bond angles, and other topological properties of compound 2 were compared with the DFT calculated results, the comparison showed good agreement with each other with varying level deviations. The energy levels of HOMO and LUMO, as well as the global chemical reactivity descriptors of representative compound 2, have been presented. A discussion of the Hirshfeld surface analysis of compound 2 has been carried out to provide insight into its structural properties.

A concise metal-free synthesis of xanthene derivatives mediated by achiral 2-aminophenol under solvent-free conditions

An efficient green technique has been developed for the synthesis of some biologically active 12-aryl or 12-alkyl 8,9,10,12-tetrahydrobenzo[a]xanthenes-11-one and 3,3,6,6-tetramethyl-3,4,5,6,7,9-hexahydro-1H-xanthene-1,8(2H)-dione derivatives have been described. This process arranged a three-component one-pot condensation of aldehydes, 2-naphthol, and dimedone mediated by 2-aminophenol and has offered an excellent scope of tailoring a large number of xanthene derivatives with good to charming yields. Short reaction time, straightforward, easy product isolation technique, non-toxic catalyst, and above all metal-free process are noteworthy advantages of this method.

Microwave-Assisted Chemistry: New Synthetic Application for the Rapid Construction of 1H-Pyrazolo[1,2-b]Phthalazine-5,10-Dione Derivatives in Diisopropyl Ethyl Ammonium Acetate

In the frame of research that examines the use of task-specific ionic liquids (ILs) for developing green methodologies toward bioactive substituted 1H-pyrazolo[1,2-b]phthalazine-5,10-diones derivatives via one-pot condensation of aldehydes, malononitrile and phthalhydrazide presence of Diisopropyl Ethyl Ammonium Acetate (DIPEAc-IL) as catalyst under conventional reflux as well as microwave irradiation condition. providing the desired product in very satisfactory yields (up to 94%) and high purity after simple workup. The task-specific ILs were recycled and reused four times without a noticeable decrease in their catalytic activity. Mild conditions with excellent conversions and simple product isolation procedures are noteworthy advantages of this method. The recyclability of the ionic liquid makes this protocol environmentally benign.

“2-Amino glucose” as a substrate for synthesis of magnetically recoverable nanocatalyst NiFe2O4@SiO2@amino glucose for the green synthesis of novel bis (1,2-dihydro-4-hydroxy-2-oxoquinolin-3-yl)methanes

2-Amino glucose ((2S,3R,4S,5S,6R)-2-amino-6-(hydroxymethyl)tetrahydro-2H-pyran-3,4,5-triol) as a substrate for the synthesis of NiFe2O4@SiO2@amino glucose supply an environmentally friendly procedure for the synthesis of bis(1,2-dihydro-4-hydroxy-2-oxoquinolin-3-yl)methanes through one-pot condensation of aldehyde or pyrazolo carbaldehyde and two equivalents of 4-hydroxyquinolin-2(1H)-ones in aqueous media. Eco‐friendliness, high purity of the desired products, short reaction time and easy workup procedure can be mentioned as the other advantages of this method. The structures of the synthesized 4-hydroxy-2(1H)-quinolone compounds were confirmed by 1H, 13C NMR and FTIR spectral data and elemental analyses.

Synthesis of 1-(benzothiazolylamino)phenylmethyl-2-naphthols accelerated by a novel magnetic nanocatalyst

4-(4-Propylpiperazine-1-yl)butane-1-sulfonic acid-modified silica-coated magnetic nanoparticles have been synthesized via covalent grafting of piperazine on (3-chloropropyl) triethoxysilane-functionalized magnetic nanoparticles through ring opening reaction of 1,4-butane sultone. The prepared reagent was characterized using different types of methods, including infrared spectroscopy (FT-IR), X-ray diffraction, thermogravimetric analysis, and scanning electron microscopy. After characterization, the catalytic activity of this reagent in the preparation of 1-(benzothiazolylamino) phenylmethyl-2-naphthols via one-pot condensation of aldehydes, 2-aminobenzothiazole, and 2-naphthol was studied in the absence of solvent. All reactions were performed under mild conditions in excellent yields during short reaction times. Using this method, the catalyst can be easily isolated from the reaction mixture by magnetic decantation using an external magnet and reused at least seven times without significant degradation in its activity.

Nano-cellulose/BF3/Fe3O4: a magnetic bio-based nano-catalyst for the synthesis of pyrimido[2,1-b]benzothiazoles under solvent-free conditions

Nano-cellulose/BF3/Fe3O4 is a bio-based and eco-friendly catalyst with high catalytic activity. Easy separation with an external magnet and recyclability without significant loss of its activity are some advantages of this catalyst. Nano-cellulose/BF3/Fe3O4 was characterized by Fourier transform infrared spectroscopy, field emission scanning electron microscopy, transmission electron microscopy, X-ray diffraction, X-ray fluorescence, vibrating sample magnetometry, thermogravimetric analysis, and BET theory. The catalyst was applied for the synthesis of 4H-pyrimido[2,1-b]benzothiazole derivatives via one-pot condensation of aldehydes, 2-aminobenzothiazol and ethyl acetoacetate, under solvent-free conditions at 100 °C. This method offers several advantages including easy work-up, excellent yields and short reaction time.

CoFe2O4@SiO2/PrNH2 nanoparticles as highly efficient and magnetically recoverable catalyst for the synthesis of 1,3-thiazolidin-4-ones

ABSTRACTAn efficient three-component synthesis of 1,3-thiazolidin-4-ones is described by one-pot condensation of aldehydes, aromatic amine and thioglycolic acid with nano-CoFe2O4@SiO2/PrNH2 as a robust heterogeneous catalyst. The significant advantages of this protocol are the use of magnetically recoverable catalyst, high to excellent product yields, operational simplicity and the use of CoFe2O4@SiO2/PrNH2 nanoparticles as an environment-friendly catalyst.

One-pot sonochemical synthesis of 1,3-thiazolidin-4-ones using nano-CdZr4(PO4)6 as a robust heterogeneous catalyst

An efficient three-component synthesis of 1,3-thiazolidin-4-ones is described by one-pot condensation of aldehydes, aniline and thioglycolic acid with nano-CdZr4(PO4)6 as a robust heterogeneous catalyst under ultrasonic irradiation. Use of simple and readily available starting materials, experimental simplicity, applying the sonochemical methodology as an efficient method and innocuous means of activation in synthetic chemistry are some advantages of this protocol.

Li(glycine)(CF3SO3) as an effective and recoverable catalyst for the preparation of 3,4-dihydropyrimidine-2-(1H)-one under solvent-free conditions

An efficient solvent-free protocol for the synthesis of 3,4-dihydropyrimidine-2-(1H)-one by the one-pot condensation of aldehyde, ethyl acetoacetate and urea using Li(glycine)(CF3SO3) as a reusable acidic ionic liquid is reported. These reactions have the advantages in this work of clean reaction, simple purification, short reaction time and high yields.

Poly(4-vinylpyridinium)hydrogensulfate as an efficient and convenient catalyst for a three-component synthesis of 7-methyl-10-aryl-10H-5,8-dioxa-benzo[b]fluoren-9,11-diones

A simple and facile synthesis of 7-methyl-10-aryl-10H-5,8-dioxa-benzo[b]fluoren-9,11-dione derivatives was accomplished via a one-pot condensation of aldehydes, 4-hydroxy-6-methylpyran-2-one, and 2H-indene-1,3-dione at 80 °C under solvent-free conditions in the presence of poly(4-vinyl)pyridinium hydrogen sulfate as a solid acid catalyst. This method has several advantages including high yield of products, shorter reaction times, simple work-up, and cleaner reaction profile.

ChemInform Abstract: Efficient One‐Pot Synthesis of β‐Acetamido Carbonyl Compounds Using Fe3O4 Nanoparticles.

A new, one-pot condensation of aldehydes, enolizable ketones and esters, AcCl, and MeCN, in the presence of Fe3O4 nanoparticles (nano-Fe3O4) as an efficient catalyst, for the preparation of β-acetamido carbonyl compounds at room temperature is described.

Efficient, one-pot synthesis of xanthene derivatives using boron sulphonic acid as a solid heterogeneous catalyst under solvent-free conditions

An efficient, convenient and green method has been introduced for the synthesis of biologically active xanthene derivatives through a one-pot condensation of aldehydes, 2-naphthol, and dimedone/naphthols in the presence of boron sulphonic acid (B(HSO4)3) as an efficient heterogeneous reusable solid acid catalyst under solvent-free conditions with good to excellent yields. Different types of aromatic and aliphatic aldehydes were used in the reaction and in all cases the products synthesized successfully. In addition, short reaction times, straightforward procedure, non-toxicity, and reusability of the catalyst are other noteworthy advantages of the present method.

Efficient One‐Pot Synthesis of β‐Acetamido Carbonyl Compounds Using Fe3O4 Nanoparticles

AbstractA new, one‐pot condensation of aldehydes, enolizable ketones and esters, AcCl, and MeCN, in the presence of Fe3O4 nanoparticles (nano‐Fe3O4) as an efficient catalyst, for the preparation of β‐acetamido carbonyl compounds at room temperature is described.

ChemInform Abstract: A Mild, Efficient, and Environmentally Friendly Synthesis of N,N′‐Arylidene Bisamides Using B(HSO4)3 under Solvent‐Free Conditions.

A green, efficient, and rapid procedure for the synthesis of N,N′-arylidene bisamide derivatives has been developed by one-pot condensation of aldehydes and amides in the presence of tris(hydrogensulfato)boron as a highly effective heterogeneous catalyst under solvent-free conditions at 100 °C. Various aromatic aldehydes, acetamide or benzamide were used in the reaction, and in all cases the desired products were synthesised successfully. This method has the advantages of high yields, a clean reaction, an environmental friendly procedure, easy workup, simple methodology, and short reaction times. .

A mild, efficient, and environmentally friendly synthesis of N,N′-arylidene bisamides using B(HSO4)3 under solvent-free conditions

A green, efficient, and rapid procedure for the synthesis of N,N′-arylidene bisamide derivatives has been developed by one-pot condensation of aldehydes and amides in the presence of tris(hydrogensulfato)boron as a highly effective heterogeneous catalyst under solvent-free conditions at 100 °C. Various aromatic aldehydes, acetamide or benzamide were used in the reaction, and in all cases the desired products were synthesised successfully. This method has the advantages of high yields, a clean reaction, an environmental friendly procedure, easy workup, simple methodology, and short reaction times. .

Efficient Synthesis of 1-Amidoalkyl-2-Naphthols by One-Pot, Three-Component Reaction under Solvent-Free Conditions

Two efficient and direct procedures have been developed for the preparation of 1-amidoalkyl-2-naphthols by a one-pot condensation of aldehydes, 2-naphthol, and amides in the presence of trichloroacetic acid or cobalt (II) chloride as catalyst. The reactions were carried out under solvent-free media. High yields, short reaction times, easy workup of the catalyst are advantages of these procedures.

Silica immobilized nickel complex: An efficient and reusable catalyst for microwave-assisted one-pot synthesis of dihydropyrimidinones

Abstract Dihydropyrimidinones (DHPM's) have been prepared by one-pot condensation of aldehydes, urea and 1,3-dicarbonyl compounds in presence of covalently anchored nickel complex on silica as catalyst in microwave under solvent-free conditions. The prepared catalyst was characterized by elemental analysis, BET surface area, atomic absorption spectroscopy (AAS), FT-IR spectroscopy and 13C CPMAS spectral studies. This method in comparison to previously reported methods offers high yields, eliminates the use of organic solvents, reduces reaction time from several hours to few minutes and also the catalyst can be reused without appreciable loss in catalytic activity.

Facile and Green Synthesis of 1,4-Dihydropyridine Derivatives in n-Butyl Pyridinium Tetrafluoroborate

l,4-Dihydropyridine derivatives were synthesized from the one-pot condensation of aldehydes, acetoacetates, and ammonium acetate in room-temperature ionic liquid n-butyl pyridinium tetrafluoroborate ([BPy][BF4]). Compared with classical Hantzsch reaction conditions, this new method has the advantage of excellent yields, short reaction time, and easy workup. The recovered ionic liquid could be recycled for at least five runs without losing its activity.

Preparation of Silica-Based Ionic Liquid an Efficient and Recyclable Catalyst for One-Pot Synthesis of α-Aminonitriles

Preparation of N-(3-silicapropyl) imidazolium hydrogen sulfate ([Sipim]HSO4) as a heterogeneous acidic ionic liquid is described. This heterogeneous ionic liquid was used as catalyst for the synthesis of α-aminonitriles by a one-pot condensation of aldehydes, amines, and trimethylsilyl cyanide at room temperature. Catalyst could be recycled for several times without any additional treatment. A simple and efficient procedure for the preparation of silica-based acidic ionic liquid ([Sipim]HSO4) is described. This heterogeneous solid acid is employed as a catalyst for the synthesis of a-amino nitriles at room temperature.

One-Pot, Three-Component Synthesis of 1,4-Dihydropyridines in PEG-400

A series of Hantzsch 1,4-dihydropyridines were synthesized by one-pot condensation of aldehyde, β-dicarbonyl compound, and ammonium acetate in polyethylene glycol (PEG-400) at 90 °C. This method has the advantages of good yields, less pollution, and simple reaction conditions.