161374-07-8

Cu(ClO4)6H2O efficiently catalyzes the three-component Biginelli reaction of aldehyde,-dicarbonyl compounds, and urea or thiourea under solvent-free conditions to afford the corresponding 3,4-dihydropyrimidin-2(1H)-ones in excellent

Metal triflimides such as Ni(NTf2)2, Cu(NTf2)2 and Yb(NTf2)3 catalyzed the Biginelli reaction to afford 3,4-dihydropyrimidin-2(1H)-ones more efficiently in pure water at room temperature th

3,4-Dihydropyrimidin-2(1H)-ones were synthesised in high yields by one-pot three-component Biginelli condensation in the presence of room temperature ionic liquids such as 1-n-butyl-3-methylimidazolium tetrafluoroborate (BMImBF4) or hexafluorop

The invention discloses a synthesis method of a dihydropyrimidone compound, which belongs to the technical field of organic synthesis, and comprises the following steps: by taking benzaldehyde or a derivative thereof, ethyl acetoacetate or acetylacetone a

A novel carbohydrate-based catalytic composite was prepared through covalent decoration of cross-linked chitosan beads with a cyclodextrin nanosponge. In this regard, chitosan beads were fabricated and cross-linked with glutaraldehyde. Subsequently, they

Deep eutectic solvents formed from hydrated metal chlorides and hydrogen bond donors (Type 4) were prepared and their catalytic activity was compared for the synthesis of dihydropyrimidinones/thionesviaBiginelli reaction at room temperature. The one-pot m

A quinoline-linked and ionic liquid-decorated covalent organic framework was prepared by incorporation of a multicomponent Povarov reaction and postsynthetic modification. The imidazolium and sulfonic acid-decorated COF-IM-SO3H can be a highly efficient B

The aim of this research was to develop a procedure for the synthesis of 3,4-dihydropyrimidin-2(1H)-ones under environmentally friendly conditions using alcohols as the starting materials in aqueous media. The developed protocol resulted in 3,4-dihydropyrimidin-2(1H)-ones derivatives, which are relevant intermediates with therapeutic and pharmacological properties. Target products were synthetized in a tandem process, which meets the requirements of pharmaceutical chemistry. The influence of the reaction conditions was investigated, and as a result, various substituted 3,4-dihydropyrimidin-2(1H)-ones were obtained with a yield of up to 81percent, free from heavy metal impurities.

Three new metal coordination complexes, namely, [Co (DPE)(H2O)4](DPE)(BS)2 (1), [Co (DPE)2(H2O)4](ABS)2 (2), [Co (DPE)(H2O)4](MBS)2(CH3/sub

Natural dolomitic limestone (NDL) is employed as a heterogeneous green catalyst for the synthesis of medicinally valuable benzimidazoles, dihydropyrimidinones, and highly functionalized pyridines via C–N, C–C, and C–S bond formations in a mixture of ethan

A simple, efficient, cost-effective, recyclable and green approach has been developed for the synthesis of new dihydropyrimidinone analogs via the Biginelli reaction. The methodology involves a multicomponent reaction catalyzed by "HPA-Montmorillonite-KSF"as a reusable and heterogeneous catalyst. This method gives an efficient and much improved modification of the original Biginelli reaction, in terms of yield and short reaction times under solvent free conditions. All the derivatives were subjected to cytotoxicity screening against a panel of four different human cancer cell lines viz. colon (Colo-205), prostate (PC-3), leukemia (THP-1) and lung (A549) to check their effect on percentage growth. MTT [3-(4,5-dimethylthiazol-yl)-diphenyl tetrazoliumbromide] cytotoxicity assay was employed to check IC50 values. Of the synthesized analogs, 16a showed the best activity with IC50 of 7.1 ± 0.8, 13.1 ± 1.4, 13.8 ± 0.9 and 14.7 ± 1.1 μM against lung (A549), leukemia (THP-1), prostate (PC-3) and colon (Colo-205) cancer lines, respectively. The 16a analog was further checked for its effect on cancer cell properties through clonogenic (colony formation) and scratch motility (wound healing) assays and thereby was found that it reduced both the colony formation and migratory properties of the lung cancer cell line (A549). Further, molecular docking studies were performed with 16a to show its binding mode. This journal is

Heterocyclic compounds with biological and pharmacological activates like 3,4-dihydropyrimidin-2-(1H)-ones and 1,4-dihydropyridines have attracted great interest. Boehmite nanoparticles functionalized with silylpropyl sulfamic acid (BNPs?SiO2(C

Abstract: A remarkably simple synthetic method has been described for the access of structurally diverse 3,4-dihydropyrimidin-2(1H)-ones in excellent yields in the presence of 2,4,6-trichloro-1,3,5-triazine (TCT) as an efficient source of hydrochloric aci

This paper deals with the study of mechanism of the Biginelli reaction using low melting mixture as solvent and catalyst. The catalytic effect of low melting mixture and the reaction mechanism is discussed on the basis of nuclear magnetic resonance (NMR)

Background: Biginelli reaction is one of the most important multiple-component chemical reactions which creates 3,4-dihydropyrimidin-2(1H)-ones. Even though Biginelli reaction was reported over a century using different substrates, literature lacks the ex

The invention discloses green catalytic Biginelli reaction, and discloses a method for synthesizing 3, 4-dihydropyrimidine-2 (1H)-ketone and derivatives thereof by the aid of 'one-pot processes'. Resin D732 is used as a catalyst, ethyl alcohol is used as a solvent, and the usage of the catalyst is 0.2g/1mmoL aldehyde. The method includes carrying out reflux reaction at the temperatures of 78 DEG Cfor 1-5 hours; filtering out the resin after the reaction is completely carried out; cooling filter liquor by the aid of ice water and then carrying out filter, ethyl alcohol re-crystallization and drying to obtain pure products. Compared with the traditional methods for synthesizing 3, 4-dihydropyrimidine-2 (1H)-ketone by the aid of acid used as a catalyst, the method has the obvious advantagesthat reaction conditions are mild, the method is high in efficiency, short in time and easy to operate, only few byproducts can be generated, and the products have good colors and are high in purity;particularly, the resin D732 used as the catalyst is low in cost, easy to prepare, store and transport and good in repeatability, is easily available and is green and environmentally friendly, accordingly, the method has an excellent industrial application prospect, and the like.

Catalytic synthesis of 3,4-dihydropyrimidin-2(1H)-ones/thiones was efficiently promoted by as little as 2.5?mol% of Br?nsted acidic ionic liquid [(CH2)3SO3HMIM]HSO4 catalyst loading via rapid heating ways. Inter

The invention provides a novel triphenyl organic bismuth (V) complex catalyst I, a preparation method thereof, and a synthesis method for nitrogen-containing compounds II-V under the catalysis of the novel triphenyl organic bismuth (V) complex catalyst I. The complex I is a cation-type organic bismuth complex, and the molecular formula is Ph3BiX2 (X=OSO2C4F9, OSO2C6F5, OSO2C8F17). The bismuth atom in the complex is connected with three triphenyls to show pentavalence. The other two perfluorooctane sulfonate roots and the cation part of the complex form an ionic bond. The synthesis method is used for synthesizing four types nitrogen-containing compounds, including bis(indolyl)methane II, dihydropyrimidinone III, dihydropyridine IV and beta-alkamine V, by taking the triphenyl organic bismuth compound as a catalyst and a conventional organic solvent as a reaction solvent. The method has the advantages of lower cost, high yield, simplicity and convenience in operation, zero pollution, repeated use of the catalyst and the like, and creates a cheap and environment-friendly way for preparing the nitrogen-containing compounds.

A series of MCM-41 supported functionalized ionic liquids doped with copper species were prepared, characterized and evaluated as catalysts in the Biginelli reaction. Most of these supported ionic liquids perform well in the reaction, especially the multifunctional copper coordinated MCM-41 supported heterogeneous catalysts (0.5)IL-TiCl5@MCM-41@Cu(15) and (0.5)IL-HSO4@MCM-41@Cu(15). The catalytic tests revealed that (0.5)IL-HSO4@MCM-41@Cu(15) was the best and powerful catalyst in the Biginelli reaction for the preparation of 3,4-dihydropyrimidinones with high to excellent yields. The catalyst can be easily separated from the reaction mixture by filtration and reused in six consecutive cycles without significant loss in catalytic activity.

The synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives was accomplished efficiently via a three-component reaction between ethyl acetoacetate, various types of aldehydes, and urea in the presence of 10 mg SO3H@imineZCMNPs as a novel, envir

BiVO4-NPs can be used as an efficient and reusable nano-catalyst for the promotion of the synthesis of biscoumarins, bis(indolyl)methanes and 3,4-dihydropyrimidin-2(1H)-ones (thiones) derivatives. The structures of the products were characteriz

The invention discloses a kind of ethanol to promote two chlorine two luxuriant titanium high-efficiency catalytic preparation of 3, 4 - dihydro pyrimidine - 2 - one derivatives of the method, the method to benzopyrone, β - diketone and the urea is used as the raw material, using ethanol as solvent and accelerator, to two chlorine two luxuriant titanium as catalyst, two chlorine two luxuriant titanium in ethanol under the synergy, can be efficient, high yield process for preparing 3, 4 - dihydro pyrimidine - 2 - one derivatives. The use amount of the catalyst used in the invention, cheap, non-toxic, stable for air, mild reaction conditions, time is short, the operation is simple, the atom economy is high, only after the end of the reaction the product through the simple column chromatography separation, to obtain 3, 4 - dihydro pyrimidine - 2 - one derivatives, for 3, 4 - dihydro pyrimidine - 2 - one derivatives of the preparation has opened up a new low-cost and green high-efficient ways of, it has broad application prospects. (by machine translation)

The present invention belongs to the technical field of organic synthesis, and discloses a synthesis method of a 3,4-dihydropyrimidin/thinatoheterocyclic compound. According to the synthesis method, an xylose acid is used as a catalyst to catalyze a reaction among aromatic aldehyde, a beta-carbonyl compound and urea or thiourea, thereby producing the 3,4-dihydropyrimidin/thinatoheterocyclic compound. According to the synthesis method provided by the prevent invention, the xylose acid is used as the catalyst, and the reaction is performed without a solvent. The method has advantages of being high in availability of raw materials, simple in process, mild in reaction condition, high in yield, and green and environmentally friendly. Furthermore, the synthesis method provided by the prevent invention is wide in substrate applicability, can synthesize a plurality of 3,4-dihydropyrimidin/thinatoheterocyclic compounds by using different substrates, and has a wide application prospect.

A novel and green approach was adopted for the synthesis of 3,4-dihydropyrimidin-2(1H)-one/thiones derivatives using Punica granatum peel as an inexpensive, efficient and mild catalyst under solvent-free condition. The methodology is characterized by high

A multicomponent Biginelli reaction in a solvent-free conditions catalyzed by 1-methyl-2-oxopyrrolidinium perchlorate ionic liquid was studied. The сondensation of aromatic aldehydes, urea (thiourea), and acetoacetic ester yielded substituted 5-ethoxycarb

A highly efficient and facile procedure for the one-pot three-component synthesis of 3,4-dihydropyrimidin-2-(1H)ones/thiones from the one-pot condensation of aldehyde, β-dicarbonyl compound and urea/thiourea was developed. The methodology is applicable to

Background: 3,4-Dihydropyrimidin-2(1H)-one derivatives are an important class of nitrogen heterocycles. These compounds present a wide range of biological activities viz antibacterial, antifungal, and antidiabetic. Although many synthetic methods are available in the literature for the synthesis of these molecules, many of these methods have their own limitations such as use of excess of expensive catalyst and poor yields. Methods: The synthesis of 3,4-dihydropyrimidin-2(1H)-one derivatives is developed through the reaction of 1,2-diols, ethyl acetoacetate and urea in the presence of lead tetraacetate in dry ethanol under reflux conditions. Results: A series of 3,4-dihydropyrimidin-2(1H)-one derivatives were synthesized in good yields (82-95%) under reflux for 2-3.5 hours in ethanol solvent. The structural assignments of these compounds were made on the basis of elemental analysis and spectroscopic data. Conclusion: This protocol is an alternative to existing procedure for the synthesis of Biginelli compounds. The present methodology reduces the number of steps in total synthesis.

The invention discloses an application of a high-efficiency catalyst in catalysis of dihydropyrimidinone compounds. A synthesis method of the catalyst cobalt benzenesulfonate comprises the following steps: mixing and heating benzenesulfonic acid and an aq

The invention discloses efficient catalysts capable of catalyzing synthesis of dihydropyrimidinones. A synthetic method of the catalysts which are p-toluenesulfonic acid cobalt complexes includes mixing p-toluenesulfonic acid and an aqueous solution of cobalt nitrate hexahydrate at 120 DEG C, heating to 120 DEG C, 5 h later, cooling to 100 DEG C at a speed of 5 DEG C per hour, filtering, and allowing crystals to be separated out of filtrate, and the crystals are the catalysts which are p-toluenesulfonic acid cobalt complexes. Structures of the catalysts are determined by utilizing X rays. The catalytic yield of the dihydropyrimidinones through catalysis with the catalysts is 98%. The p-toluenesulfonic acid cobalt complexes have advantages of short reaction time, a low catalyst using amount, simple operation steps, and the like, and the method is a green synthetic method.

Three new metal coordination complexes, namely [Co(BPY)2(H2O)2](BPY)(BS)2(H2O)4 (1), [Co(BPY)2(H2O)4](ABS)2(H2O)2 (2) and [Co(BPY)(H2O)4](MBS)2 (3) (BPY?=?4,4′-bipyridine, BS?=?phenylsulfonic acid, ABS = p-aminobenzenesulfonic acid, MBS?=?p-methylbenzenesulfonic acid), were obtained under hydrothermal conditions. Complexes 1, 2, 3 were structurally characterized using single-crystal X-ray diffraction and infrared spectroscopy. All of them display low-dimensional motifs: complex 1 displays a two-dimensional structure; and complexes 2 and 3 exhibit a one-dimensional tape structure. Through strong intermolecular hydrogen bonding interactions and weak packing interactions, all of them further stack to generate a three-dimensional supramolecular architecture. Catalysts 1, 2, 3 were involved in the green synthesis of a variety of 3,4-dihydropyrimidin-2(1H)-ones under solvent-free conditions through Biginelli reactions. The corresponding catalytic product was obtained in quantitative yields (99%) under eco-friendly synthesis conditions for the variety of reactions. Catalysts 1, 2, 3 exhibit excellent efficiency for the desired product, and their catalytic performance shows the following order: 2?>?1?≈?3, which can be ascribed to the hydrophobic interactions of different phenylsulfonate groups. The catalytic performance for the Biginelli reaction is not only dependent on the selected solvents, but also inversely proportional to the polarities of the solvents. Copyright

In this paper, a novel SO3H-containing ionic liquid namely N,N-diethyl-N-sulfoethanaminium hydrogen sulfate ([Et3N-SO3H]HSO4) has been synthesized, and characterized by studying its FT-IR, 1H NMR, su

1-Ethyl-3-methylimidazolium ethyl sulfate was synthesized and its supported ionic liquid phase form was prepared and used as an organocatalyst for the synthesis of substituted piperidinones and 3,4-dihydropyrimidinones. The ionic liquid was characterized by 1H NMR, 13C NMR, and mass spectrometry. The catalyst is novel, stable, completely heterogeneous, and recyclable for several times and can be easily recovered by filtration. It was characterized with scanning electron microscopy, transmission electron microscopy, thermogravimetric analysis, and energy-dispersive X-ray spectroscopy techniques. The workup procedures are very simple, and products were obtained in good-to-excellent yields with reasonable purities without the need for further chromatographic purification.

Nano-ZrO2 sulfuric acid [n-ZrO2-SO3H (n-ZrSA)] has been synthesized from the reaction of nano-ZrO2 with chlorosulfonic acid as sulfonating agent. This catalyst was characterized via FT-IR, XRD, TGA, FESEM, TEM,

Triphenyl bismuth bisperfluorooctanesulfonate is an air- and water-stable Lewis acid. It exhibits high catalytic efficiency for the synthesis of nitrogen heterocycles such as diindolylmethane derivatives, dihydropyrimidinones, dihydropyridines and 1,2-disubstitued benzimidazoles under mild condition. Furthermore, it can be reused without loss of activity in a test of five cycles.This catalytic system affords a simple and efficient way for the synthesis of N-containing compounds.

A novel copper-ethylenediamine tetracarboxylate modified core-shell magnetic catalyst is introduced. The prepared catalyst was fully characterized by various spectroscopic analyses such as XRD, SEM, FT-IR, EDX, ICP, and CHNOS. After characterization, its

The Biginelli reaction of β-ketoesters with aryl aldehyde and urea or thiourea in the presence of a Keplerate type giant nanoporous isopolyoxomolybdate, (NH4)42[Mo72 VIMo60 VO372

Three new metal coordination polymers, namely, [Co(DPP)2(H2O)2]·(BS)2·2H2O (1), [Co(DPP)2(H2O)2]·(ABS)2·2H2O (2) and [Co(DPP)2(MBS)su

We report here an efficient and green method for Biginelli condensation reaction of aldehydes, β-ketoesters and urea or thiourea catalyzed by Br?nsted acidic ionic liquid [Btto][p-TSA] under solvent-free conditions. Compared to the classical Biginelli rea

Tris(pentafluorophenyl)borane catalyzed, one-pot, simple, efficient and environmentally benign protocol for the synthesis of dihydropyrimidinones/thiones via Biginelli reaction has been described. The main highlights of the present protocol is low catalys

An efficient and green route for the synthesis of dihydropyrimidinones via microwave-assisted Biginelli reaction catalyzed by 3 mol% of heteropolyanion-based ionic liquids under solvent-free conditions has been reported. The practical reaction was found t

Zirconocene bis(perfluorobutanesulfonate) is air- and water-stable and proved to be ionic on basis of conductivity measurements. It exhibits high catalytic efficiency for the synthesis of N-heterocyclic compounds under solvent-free condition, such as benzimidazoles, benzodiazepines, dihydropyrimidinones and dihydropyridines under mild condition. Furthermore, it can be reused without loss of activity in a test of five cycles. This catalytic system affords a simple and efficient approach for the synthesis of N-heterocyclic compounds.

A simple and effective synthesis of 3,4-dihydropyrimidin-2(1H)-one and thione derivatives has been developed in the presence of nano cobalt manganese oxide as catalyst under thermal solvent-free conditions. The proposed procedure ensures easy to handle, r

A simple, highly efficient and ecofriendly approach for the preparation of biologically potent pyranopyrazoles and 3,4-dihydropyrimidin-2(1H)-ones are described here. A Ti-grafted polyamidoamine dendritic silica hybrid catalyst was successfully synthesize

We report here an understanding of systems chemistry on small molecules through covalent mechanochemistry. As a proof-of-concept, the multicomponent Biginelli reaction by subcomponent synthesis was considered as a model system. Reactions were performed un

The catalytic application of a novel manganese-containing periodic mesoporous organosilica with ionic-liquid framework (Mn@PMO-IL) in the Biginelli reaction was investigated. First, the Mn@PMO-IL nanocatalyst was prepared and characterized by TEM, SEM, X-

A solvent free three component condensation reaction between an aldehyde, ethyl acetoacetate and urea catalyzed by graphite, a green catalyst is described for the synthesis of dihydropyrimidin-2(1H)-ones. This protocol is scalable and the catalyst is reus

An efficient and highly convergent route to dihydropyrimidinones (DHPMs) has been developed by one-pot threecomponent oxidative cyclocondensation of a variety of alcohols, β-ketoesters/β-oxodithioester and urea in the presence of T3Pμ/ DMSO. This new appr

One-pot three-component condensation of ethyl acetoacetate, aldehyde and urea or thiourea in refluxing ethanol in the presence of catalytic amounts of citric acid afforded the corresponding 3,4-dihydropyrimidin- 2(1H)-ones/thiones in high yields. The cata

Pyridine dicarboxylic acid guanidine-cobalt complex (PDAG-Co) (3) catalyzes one-pot, three-component coupling of aldehydes, b-dicarbonyl compounds, and ammonium acetate to afford the corresponding 1,4-dihydropyridines (1,4-DHPs) via Hantzsch reaction. 3,4

Preparative nanoZnO and ZnO have been found as reusable catalysts for either condensation or dissociation of urea to ammonia and controllable selectivity in the Biginelli and Hantzsch reactions. The feasibility of urea dissociation to ammonia and switchin

Silica gel supported bismuth nitrate pentahydrate has been shown to be an efficient catalyst for the Biginelli reaction. The main advantages of the catalyst include short reaction time and high yield of the products. This observation has been confirmed by

3,4-Dihydropyrimidinone and derivatives were synthesized by the one-pot, three-component Biginelli condensation of an aldehyde, β-dicarbonyl compound and urea. Synthesis was carried out in aqueous sodium hydroxide using Aliquat-336 as a phase transfer agent. Compared to the classical Biginelli reaction conditions, this new method cousistently has the advantage of excellent yields and short reaction time.

A simple and efficient transesterification process for the synthesis of β-ketoester derivatives has been achieved by the reaction of methyl β-ketoester with higher alcohols at 110 C under solvent-free, catalyst-free conditions and its application in synthesis of 3,4-dihydropyrimidin-2(1H)-ones C-5 ester derivatives via Biginelli reaction has been described.