64495-94-9

Upstream product

• 123-11-5 4-methoxy-benzaldehyde 
• 126-81-8 dimedone 

Downstream Products

• 1159509-39-3 C₂₂H₂₂O₅ 
• 1159509-40-6 C₂₂H₂₂O₅ 
• 1176087-43-6 7,7-dimethyl-10-(4-methoxyphenyl)-6,7,8,10-tetrahydropyrimido[5,4-b]quinoline-2,4,9(1H,3H,5H)-trione 

Relevant academic research and scientific papers

Multicomponent Synthesis of Functionalized Tetrahydroacridinones: Insights into a Mechanistic Route

A mechanistic study of three-component reactions of various aromatic amines with a number of aldehydes and 1,3-diones was achieved. The unprecedented reaction involved a nucleophilic attack of an aromatic amine on the in situ generated Michael adduct inte

A new type IV DES: a competent green catalyst and solvent for the synthesis of α,β-unsaturated diketones and dicyano compounds by Knoevenagel condensation reaction

DESs are new and greener alternatives to ionic liquids formed by mixing components that are capable of forming hydrogen bonds between them. The strong hydrogen bond interactions between the constituents make a large depression in the melting points compared to pure constituents. They are emerging as green solvents and have loomed as adorable alternatives to conventional organic solvents and ionic liquids with unique properties. In the present article, four new CeCl3·7H2O-based DESs were developed and their physical properties were studied. Their activities were checked in the Knoevenagel condensation reaction of dimedone/malononitrile with various aldehydes. The recyclability of the catalyst/solvent was achieved up to five runs without much change in the activity.

Potassium Natural Asphalt Sulfonate (K-NAS): Synthesis and characterization as a new recyclable solid basic nanocatalyst and its application in the formation of carbon–carbon bonds

In this research, we synthesized and characterized a new heterogeneous basic nanocatalyst and its catalytic application was studied in the Claisen-Schmidt and Knoevenagel condensations. In order to prepare this nanocatalyst, first, the Iranian natural asphalt was sulfonated with the concentrated sulfuric acid and then, converted to the potassium natural asphalt sulfonate (K-NAS). In order to characterization of the nanocatalyst, used of FT-IR spectroscopy, scanning electron microscopy (SEM), energy dispersive spectroscopy (EDS), X-ray diffraction (XRD), inductively coupled plasma (ICP) and thermogravimetric analysis (TGA) techniques. This new basic heterogeneous nanocatalyst have advantages such as being eco-friendly, huge specific surface area, high reactivity and recyclability.

Synthesis of heterocyclic compounds derived from dimedone and their anti-tumor and tyrosine kinase inhibitions

The reaction of dimedone with arylaldehydes gave the benzylidene derivatives 3a-c, the latter underwent a series of heterocyclization reactions to give fused thiophene, pyrazole isoxazole and pyridazine derivatives. The synthesized compounds were evaluated against different kinds of cancer cell lines together tyrosine kinases and Pim-1 kinase inhibitions. All the synthesized compounds were assessed for the inhibitory activities against A549 (non-small cell lung cancer), H460 (human lung cancer), HT-29 (human colon cancer) and MKN-45 (human gastric cancer) cancer cell lines together with foretinib as the positive control by a MTT assay. The promising compounds were 3c, 5b, 5e, 5f, 7c, 7f, 9c, 11b, 12c, 12d, 13b, 13d, 14b, 16c and 16d among the tested compounds. On the other hand, compounds 5b, 5e, 5f, 7c, 11b, 12c, 12d, 13d, 14b, 16c and 16d were the most effective inhibitors against tyrosine kinases and compounds 5b, 11b, 12d, 13d, 14b and 16c were the most potent against Pim-1 kinase.

Simple Protocol for the Knoevenagel Condensation under Solvent Free Conditions using Tungstophosphoric Acid as Catalyst

The effect of calcination on the performance of tungstophosphoric acid for the product of Knoevenagel condensation was investigated. Substituted aldehydes and dimedone has been used in the presence of calcined tungstophosphoric acid as a heterogeneous catalyst using grinding method at room temperature. The results of reactions revealed that calcined tungstophosphoric acid has superior catalytic activity comparing to non-calcined catalyst in terms of yield and reaction time. Maximum yield of model compound was achieved by using 10 mol% of calcined catalyst in a reaction time that does not exceed 10 min, whereas the yield at same amount of non-calcined catalyst was 86 % in a reaction time of 35 min.

A Novel Mechanistic Study on Ultrasound-Assisted, One-Pot Synthesis of Functionalized Benzimidazo[2,1-b]quinazolin-1(1H)-ones

Ultrasound-assisted synthesis of benzimidazo[2,1-b]quinazolin-1(1H)-ones was achieved via piperidine-catalyzed three-component reaction of 2-aminobenzimidazoles, an aromatic aldehyde, and 1,3-dione in aqueous isopropanol. This mechanism was first suspected following our identification of unusual reaction intermediates in a one-pot reaction. An unprecedented coupling reaction, it involved a nucleophilic attack by 2-aminobenzimidazole on in situ generated Michael adduct, followed by electrocyclic ring formation reaction. In contrast to the commonly accepted mechanism, that the direct reaction of 2-amino benzimidazole with a Knoevenagel adduct cannot deliver target compounds.

One-pot multi-component synthesis of polyhydroquinolines at ambient temperature

An efficient and eco-friendly one-pot synthesis of polyhydroquinolines at ambient temperature from the multi-component reaction of aldehyde, 1,3-diketone, β-keto ester and ammonium acetate in ethanol medium is described. The probable mechanism of transformation is suggested. The features of this procedure are mild reaction conditions, no need of external catalyst, good yields and the operational simplicity at ambient temperature.

Domino Knoevenagel condensation, Michael addition, and cyclization using ionic liquid, 2-hydroxyethylammonium formate, as a recoverable catalyst

The Knoevenagel condensation reaction of aromatic aldehydes with malononitrile or dimedone was investigated. Also, the three-component and one-pot synthesis of 2-amino-5-oxo-4-aryl-4,5-dihydropyrano[3,2-cchromene-3- carbonitrile derivatives by condensing

Uncatalysed Knoevenagel condensation in aqueous medium at room temperature

Knoevenagel condensation of various aromatic and heteroaromatic aldehydes with active methylene compounds like malononitrile, ethyl cyanoacetamide, ethyl cyanoacetate, barbituric acids, Meldrum's acid, dimedone and pyrazolone proceeds smoothly with stirring in an aqueous medium. The reactions occur at room temperature giving excellent yields of the products. The work-up procedure is very simple and the products do not require further purification.

A new one-pot synthesis of some novel haxahydroquinazoline derivatives

A one-step synthesis of 2-amino-4-aryl-7,7-dimethyl-3,4,5,6,7,8-hexahydro-5-oxoquinazolines (4a-e) and 4-aryl-2,7,7-trimethyl-3,4,5,6,7,8-hexahydro-5-oxoquinazolines (5a-e) involving easily available 5,5-dimethyl-1,3-cyclohexanedione, aryl aldehyde, acetamidine and guanidine is described.