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An efficient method for the synthesis of a new highly substituted pyrrolidinone derivative is developed via a three-component one-pot reaction of aniline, diethyl acetylenedicarboxylate, and 4-anisaldehyde. The structure of ethyl 4-hydroxy-2-(4-methoxyphenyl)-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate is confirmed by FTIR, 1H and 13C NMR spectroscopy. Unambiguous evidence for the structure of the synthesized product is obtained from the single crystal X-ray analysis. The comparison of both its molecular structure and intermolecular interactions with the previously known analogous compounds reveals that the mutual syn- or antiperiplanar orientation of ester C=O and pyrrolinone-bound OH is related to the type of molecular dimers formed in the solid state. The geometrical structure, the HOMO–LUMO analysis (electrophilicity index), 1H and 13C chemical shifts of the desired product are also calculated by DFT at the B3LYP level with the 6-31++G(d,p) basis set. The calculated chemical shifts are in compliance with the experimental data.

Propargylamines are an important constituent of diverse, biologically active and industrially valuable compounds. These useful, convenient and effective compounds can be synthesized via the A3-coupling reactions between an aldehyde, amine, and alkyne in the presence of a catalyst. In the past years, most of the catalysts containing transition metals were applied in these reactions, but today, various heterogeneous catalysts, especially nanocatalysts are used. The purpose of this review was to introduce some modern catalysts for the A3-coupling reaction.

A clean, convenient and facile approach for one-pot ultrasonic assisted synthesis of substituted 3-pyrrolin-2-ones from diethyl acetylenedicarboxylate, aniline and aldehyde derivatives is described. The reactions were carried out in the presence of an efficient, green and reusable acidic nanocatalyst, magnetic cobalt ferrite nanoparticles functionalized with citric acid (CoFe2O4@CA), with high yields under mild conditions. Also, use of ultrasound irradiation made this approach an attractive protocol for the synthesis of these products. The method has been successful in achieving the green chemistry objective. An energy efficient protocol using ultrasound irradiation instead of conventional heating or stirring and use of ethanol as a non-hazardous, inexpensive and green solvent in the one-step reaction against sequential reaction steps thus combining the features of both economic and environmental advantages. In this research, magnetic cobalt ferrite nanoparticles functionalized with citric acid (CoFe2O4@CA) catalyzed synthesis of substituted 3-pyrrolin-2-ones under ultrasonic irradiation via a practical and environmentally benign one-pot three-component protocol.

A clean, efficient and mild method is presented for one-pot three-component synthesis of 2-amino-7,7-dimethyl-4-(4-(methylthio)phenyl)-5-oxo-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile using nickel ferrite magnetic nanoparticles as a recyclable catalyst in green solvent at 40 °C. The structure of the target product was confirmed by FT-IR, 1HNMR, 13CNMR and single crystal X-ray structure analysis. In the present work, the quantum theoretical calculations of the molecular structure of this new compound have been predicted using Density Functional Theory in the solvent DMSO. The geometries of the title compound were optimized by B3LYP/6-31+G* and B3LYP/6-311++G** levels of theory. The electronic spectrum of the title compound in the solvent DMSO was carried out by TDB3LYP/6-311++G** method. Frontier molecular orbitals, molecular electrostatic potential, electronic properties, natural charges and natural bond orbital analysis of the mentioned compound were investigated and discussed by theoretical calculations. In the present work, the frontier molecular orbitals, molecular electrostatic potential, electronic properties, natural charges and Natural Bond Orbital (NBO) analysis of the mentioned compound were investigated and discussed by theoretical calculations.

The surface of silica-coated CoFe2O4 magnetic nanoparticles (CoFe2O4@SiO2), which is resistant to the oxidation due to silicone coating, was functionalized using chlorosulfonic acid and used as an efficient and recyclable catalyst for the preparation of 3-pyrrolin-2-ones from diethyl acetylenedicarboxylate, an aldehyde and aniline in ethanol solvent at 60 °C. In the presented study, some fascinating chracteritics of such catalyst, such as magnetically separable, simple workup and obtaining a high purity of products by simple recrystallization, have been successfully obtained. The structural features of CoFe2O4@SiO2-SO3H catalyst were elucidated by X-ray powder diffraction (XRPD), thermo-gravimetric studying (TGA), scanning electron microscopy (SEM) and FT-IR spectra.

The modification of silica-coated CoFe2O4 magnetic nanoparticles (CoFe2O4@SiO2) with chlorosulfonic acid, which can be utilized as an organic-inorganic hybrid heterogeneous catalyst, introduces an astonishing and efficient system for the synthesis and simplicity of the recovery of the catalyst. The applied CoFe2O4 magnetic nanoparticles are 22.98–45.30 nm measured that can be utilized as a catalyst for the preparation of 2-amino-4,6-diarylnicotinonitrile under microwave irradiation in solvent-free conditions by four component reaction of aromatic acetophenone, aldehydes analogues, malononitrile and ammonium acetate. The so synthesized magnetic nanocatalyst was characterized by X-ray powder diffraction, SEM, TGA and FT-IR techniques. This simple protocol suggests advantages such as shorter reaction times, high yield, catalyst recovery, achieving the high purity of products by simple recrystallization and facile work-up. Other noticeable characteristics contain the catalyst can be recovered at least five times without any clear decrease in its catalytic activity.

Tetramethylguanidine supported onto magnetic Fe3O4 nanoparticles (MNPs-TMG) was prepared and identified by several techniques such as TEM, XRD, SEM, FT-IR and TGA analyses. The synthesized catalyst was utilized as an effective catalyst for aldol reaction between acetone and various aldehydes to achieve β-hydroxy carbonyl compounds in excellent yields. This procedure has several advantages, such as moderate reaction conditions, excellent yields, short reaction time and easy purification of the products. Additionally, supporting this organosuperbase catalyst on magnetic nanoparticles offers a simple method for easy reuse and recovery of the catalyst using an external magnetic field.

The crystal structures of two compounds,ethyl-(E)-2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-3-phenyl-2-propenoate and ethyl-(Z)-2-(2,3-dioxo-2,3-dihydro-1H-indol-1-yl)-3-phenyl-2-propenoate were determined from single-crystal X-ray diffraction and characterized by FT-IR, 1HNMR and 13CNMR spectroscopy. The quantum theoretical calculations for two structures were performed by density functional theory (DFT/B3LYP/6-311+G*). From the optimized structure, geometric parameters were obtained and experimental measurements were compared with the calculated data. Frontier molecular orbitals, total density of states, molecular electrostatic potential, molecular properties, thermodynamic parameters and NBO analysis for E and Z isomers were investigated by theoretical calculations.

The 1:1 imine intermediate generated by the addition of a primary amine to cyclohexanone trapped by N-isocyaniminotriphenylphosphorane (NICITPP) in the presence of aromatic carboxylic acids and the corresponding iminophosphorane intermediate was formed. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature (18-26°C). The disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields.

Reactions of N-isocyaniminotriphenylphosphorane (NICITPP) with 2-oxopropyl-1-benzenecarbothioate in the presence of aromatic carboxylic acids and primary amines proceed smoothly at room temperature...

Tetramethylguanidine-functionalized silica-coated iron oxide magnetic nanoparticles as a productive and reusable catalyst have been applied for the one-pot three-component synthesis of furanone derivatives (4a–o). In addition to the characterization of all products by FT-IR, $$^{1}\hbox {HNMR}$$ and $$^{13}\hbox {CNMR}$$ spectroscopy, single-crystal X-ray analysis of ethyl 5-oxo-2-phenyl-4-(phenylamino)-2,5-dihydrofuran-3-carboxylate product has been made. Easy recrystallization and good-to-excellent yields (81–92%) of furanone derivatives are notable characteristics of this procedure. The catalyst identification was performed using FT-IR, XRD, SEM, TEM and TGA techniques. It is worth noting that the nanocatalyst can be recycled with an external magnet and reused for several times. SYNOPSIS In this procedure, tetramethylguanidine-functionalized silica-coated iron oxide magnetic nanoparticles $$(\hbox {Fe}_{3}\hbox {O}_{4}\hbox {-TMG})$$ has been employed as an efficient, eco-friendly and reusable catalyst for one-pot three-component synthesis of furanone derivatives in a green solvent at $$40\,^{\circ }\hbox {C}$$ . The use of magnetic nanocatalyst is the superior feature of this method.

The ultrasound-promoted one-pot multicomponent synthesis of substituted 3-pyrrolin-2-ones using citric acid as a green additive in a green solvent is reported. Citric acid catalyzed the reaction efficiently without the need for any other harmful organic reagents. Clean reaction profile, easy work-up procedure, excellent yields and short reaction times are some remarkable features of this method. The utilization of ultrasound irradiation makes this method potentially very useful, fast, clean and convenient.

A convenient one-pot synthesis of coumarin derivatives from the three-component reaction of triphenylphosphine, an acetylenic ester, and a phenol (1-naphthol, 2-naphthol and benzo[1,3]dioxol-5-ol) ...

Reactions of benzoic acid derivatives and (E)-cinnamic acid derivatives with $N,N^{\prime }$ -dialkyl carbodiimide proceed smoothly at room temperature and in neutral conditions to afford N-acylurea derivatives in high yields. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions were observed.

An easy and convenient method is reported for the synthesis of polyhydroquinoline derivatives in solvent-free conditions under microwave irradiation in the presence of magnetic nickel ferrite nanoparticles (NiFe2O4 MNPs) as a catalyst. Excellent yields (82–94 %), facile work-up, achieving high purity of products via simple recrystallization, and short reaction times (2–5 min) are some advantages of this procedure. It is worth noting, the catalyst is magnetically removed without significant loss of activity for reuse a few times.

Reactions of N-isocyaniminotriphenylphosphorane with cyclopentanone in the presence of an E-cinnamic acid derivative and a primary amine proceeds smoothly at room temperature and in neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives in high yields. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions were observed.

Reactions of N-isocyaniminotriphenylphosphorane (Ph3PNNC) with aromatic bis-aldehydes (isophthalaldehyde and terphthalaldehyde) in the presence of 3-phenyl-2-propynoic acid and secondary amines proceed smoothly at room temperature and in neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives in high yields. The reaction proceeds smoothly and cleanly under mild conditions and no side reactions were observed.

The reaction of (E)-3-aryl-2-propenoic acid derivatives with (N-isocyanimino) triphenylphosphorane proceeds smoothly at room temperature to afford the corresponding 2-[(E)-2-aryl-1-ethenyl]-1,3,4-oxadiazole via an intramolecular aza-Wittig reaction in good yields under neutral conditions. The structures of the products were deduced from their IR, 1H NMR, and 13C NMR spectra and mass spectrometry. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:612–616, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20701

A single crystal X-ray structure analysis of two polymorphs of ethyl 2-(2-chlorophenyl)-4-hydroxy-5-oxo-1-phenyl-2,5-dihydro-1H-pyrrole-3-carboxylate, i.e. I (Z' = 1) and II (Z' = 4), is performed. It is shown that the molecular geometries are the same in I and II, and the same bifurcated O—H⋯O hydrogen bonds (involving hydroxyl and ester C=O groups) exist between the adjacent molecules, giving rise to molecular dimers which, however, are different in I and II: centrosymmetric (heterochiral) and homochiral, respectively.

A one-pot synthesis of alkyl 2-(2-oxo-1,2-dihydronaphtho[2,1-b]thiophen-1-yl)-2-(1,1,1-triphenyl-λ5 -phosphanylidene)acetates in fairly high yields by the reaction of 2-naphthalenethiol, dialkyl acetylenedicarboxylates and triphenylphosphine is reported. The formulas of these compounds were confirmed by IR, 1 H,31P, and 13C NMR spectroscopy. The NMR spectra indicated that solutions of the phosphorus ylides (CDCl3 as solvent) contain two rotamers (E and Z). The relative percentages of rotamers in CDCl3 for each phosphorus ylide were determined from the 31P NMR spectra.

A novel application in the field of N-isocyaniminotriphenylphosphorane (Ph3PNNC) chemistry has been introduced in this work. A series of substituted isoindolin-1-one ring systems has been successfully synthesized through a novel and efficient multicomponent reaction of methyl 2-formylbenzoate and primary amines in the presence of N-isocyaniminotriphenylphosphorane (Ph3PNNC) as a catalyst. This one-pot three component reaction (3-CR) gives high yield using N-isocyaniminotriphenylphosphorane (Ph3PNNC) as a metal-free catalyst under mild conditions.

Reaction of N-isocyaniminotriphenylphosphorane with biacetyl in the presence of a carboxylic acid in water proceeds smoothly at RT (20–26°C) and neutral conditions to afford sterically congested 1,3,4-oxadiazole derivatives in high yields. The reaction proceeds smoothly and clearly under mild conditions and no side reactions were observed.

The 1:1 imine intermediate generated by the addition of a primary amine to a cyclic ketone is trapped by N-isocyaniminotriphenylphosphorane in the presence of 3-phenyl-2-propynoic acid and the corresponding iminophosphorane intermediate was formed. Disubstituted 1,3,4-oxadiazole derivatives are formed via intramolecular aza-Wittig reaction of the iminophosphorane intermediate. The reactions were completed in neutral conditions at room temperature (18–26°C). The disubstituted 1,3,4-oxadiazole derivatives were produced in excellent yields.

New zinc(II) and mercury(II) complexes of 2,2′-diamino-4,4′-bis(1,3-thiazole) (DABTZ), [M(DABTZ)(CH3COO)2], have been synthesized and characterized by elemental analysis, IR-, 1H NMR-, 13C NMR spectroscopy and studied by thermal analysis and X-ray crystallography. The structural characterization of the [Zn(DABTZ)(CH3COO)2] complex shows the complex to be a monomer and the Zn coordinated by two nitrogen atoms of the “DABTZ” ligand and four oxygen atoms of the acetate anions.

The reaction of (E)-3-aryl-2-propenoic acid derivatives with (N-isocyanimino) triphenylphosphorane proceeds smoothly at room temperature to afford the corresponding 2-[(E)-2-aryl-1-ethenyl]-1,3,4-oxadiazole via an intramolecular aza-Wittig reaction in good yields under neutral conditions. The structures of the products were deduced from their IR, 1H NMR, and 13C NMR spectra and mass spectrometry. © 2011 Wiley Periodicals, Inc. Heteroatom Chem 22:612–616, 2011; View this article online at wileyonlinelibrary.com. DOI 10.1002/hc.20701

Crystals of the title compound, ethyl (Z)-2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)-3-phenyl-2-propenoate, C19H15NO4, Mr = 321.32 are monoclinic, space group P21/n, with a = 6.172(2), b = 8.029(2), c = 32.664(6)A, β = 91.79(3)°, V = 1617.9(7)A3 and Z = 4 at T = 100(2)K. The crystal packing is stabilized by an extensive three-dimensional system of C-H…O/π contacts with some oxygen atoms involved in trifurcated, four-centered interactions.