28746-58-9

Upstream product

• 100-52-7 benzaldehyde 
• 126-81-8 dimedone 
• 3376-23-6 N-methyl-α-phenylnitrone 

Downstream Products

• 1159509-05-3 7,8-dihydroxy-3,3-dimethyl-9-phenyl-2,3,4,9-tetrahydroxanthen-1-one 
• 1159509-06-4 5,8-dihydroxy-3,3-dimethyl-9-phenyl-2,3,4,9-tetrahydroxanthen-1-one 
• 1372100-48-5 10,10-dimethyl-7-phenyl-7,10,11,12-tetrahydro-6H-chromeno[4,3-b]quinoline-6,8(9H)-dione 
• 107752-97-6 2-amino-7,7-dimethyl-5-oxo-4-phenyl-5,6,7,8-tetrahydro-4H-chromene-3-carbonitrile 
• 1309477-28-8 10,10-dimethyl-7-phenyl-7,9,10,11-tetrahydro-6H,8H-chromeno[4,3-b]chromene-6,8-dione 
• 722483-58-1 3,7,7-trimethyl-4-phenyl-4,7,8,9-tetrahydroisoxazolo[5,4-b]quinolin-5(6H)-one 
• 1176087-22-1 7,7-dimethyl-10-phenyl-6,7,8,10-tetrahydropyrimido[5,4-b]quinoline-2,4,9(1H,3H,5H)-trione 
• 872410-93-0 2-amino-6,6-dimethyl-9-phenyl-5,6,7,9-tetrahydro[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one 
• 421586-21-2 6,6-dimethyl-9-phenyl-5,6,7,9-tetrahydro-[1,2,4]triazolo[5,1-b]quinazolin-8(4H)-one 

Relevant academic research and scientific papers

Sustainable synthesis of 1,8-dioxooctahydroxanthenes in deep eutectic solvents (DESs)

Deep eutectic solvents are obtained by the fusion of two or more compounds: hydrogen bond donors (HBDs) and hydrogen bond acceptors (HBAs). They are formed by mixing the constituents with moderate heating (via hydrogen bond interactions). In this manuscript, the dual activities (as catalysts and reaction media) of six deep eutectic solvents were compared for the synthesis of 1,8-dioxooctahydroxanthenes at room temperature. Here DES 2, a combination of ZrOCl2·8H2O with ethylene glycol at a 1 : 2 ratio, was found to be the supreme catalyst among the six DESs and was reused for five batches. The photophysical properties of the xanthene derivatives were examined by UV-vis and fluorescence spectroscopy in THF. The synthesised molecules showed absorption maxima around 285-295 nm and emission maxima around 403-404 nm. The ground state dipole moments of all the molecules were calculated by the Debye-Guggenheim method using toluene as the non-polar solvent. All the synthesised molecules showed significant dipole moment values and are in good agreement with theoretical values.

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.

Zinc-containing ionic liquid as a dual solvent-catalyst in base-free condensations under ultrasonic irradiation

In this study, natural-based ionic liquid (IL) using caffeine (Caff), trietahnolamine (TEA) and ZnBr2, [Caff-TEA]+[ZnBr3]?, which features high catalytic activity and environmentally-friendly nature was synthesized with melting point of 76?°C by a facile method. The synthesized [Caff-TEA]+[ZnBr3]? has high catalytic activity as both of catalyst and solvent in condensation reactions for the synthesis of benzylidenes, bis-hydroxyenones and xanthenes. Synthesized IL was characterized by proton nuclear magnetic resonance (1HNMR), Fourier transform infrared spectroscopy (FT-IR), X-ray diffraction (XRD) and Energy-dispersive X-ray spectroscopy (EDX) analysis. Also synthesized heterocycles were characterized by FT-IR, proton nuclear magnetic resonance (1HNMR) and carbon nuclear magnetic resonance (13CNMR).

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.

AlCl3-promoted cyclization of β-keto derivatives with in situ generated enamines under solvent-free high speed ball milling: An efficient one-pot access to polysubstituted 1,4-dihydropyridines

Under high speed ball milling (HSBM), a simple method for efficient synthesis of structurally diverse polysubstituted 1,4-dihydropyridines is developed via AlCl3-promoted Robinson-like cyclization of β-keto derivatives with in situ generated enamines. This one-pot protocol exhibits the advantages of high chemoselectivity, short reaction time, good functional group tolerance, mild reaction condition and easy work-up.

A facile, eco-friendly, proton donor-acceptor catalyzed, one-pot, three-component synthesis of tetrahydrobenzo[b]pyrans

Piperidinium acetate catalyzed, three-component cyclocondensation between aryl aldehydes (1), malononitrile (2) and cyclic-1,3-diketo compounds (3) in the eco-friendly and universal solvent water at room temperature for 0.5 h, resulted in the formation of tetrahydro[b]pyran derivatives (4). The formation of 4 could also be established in a step-wise fashion by isolating independently each of the intermediates benzylidine malononitrile 5 and benzylidine cyclohexane-1,3-dione 6 and treating them subsequently with 3 and 2, respectively to obtain benzopyrans 4. Mechanistic studies on the formation of 4 from 1, 2 and 3 are reported. Further, the synthesis of 4 could also be achieved in two variable but identical end-product giving tandem syntheses by treating 1 with 2 and then with 3 giving 4 or by treating 1 with 3 and then with 2 giving 4. All the products were suitably characterized using NMR, IR and Mass spectroscopy.

Metal-free homocoupling of 2,2-(Arylmethylene)-bis(3-hydroxy-5,5- dimethylcyclohex-2-enone) mediated by n-methylhydroxylamine

The reaction of 5,5-dimethylcyclohexane-1,3-dione with an acyclic nitrone in DMF or acetone affords a 1:1 mixture of dimer 2,2-(arylmethylene)-bis(3- hydroxy-5,5-dimethylcyclohex-2-enone) and tetramer 2,2',2'',2'''-(1,2- diarylethane-1,1,2,2-tetrayl)tetrakis(3-hydroxy-5,5-dimethyl-cyclohex-2-enone). This unprecedented type of metal-free homocoupling of two molecules of the dimer to furnish the tetramer is believed to proceed via an oxidation/reduction process involving N-methylhydroxylamine.

Fe(DS)3, an efficient Lewis acid-surfactant-combined catalyst (LASC) for the one pot synthesis of chromeno[4,3-b]chromene derivatives by assembling the basic building blocks

A highly efficient multicomponent heteroannulation protocol for the synthesis of a library of chromeno[4,3-b]chromene derivative has been developed by applying a Lewis acid-surfactant-combined catalyst (LASC) [Fe(DS) 3]. The LASC converted the initially floating reaction mass into a homogeneous mixture, which on stirring became a turbid emulsion of colloidal aggregates. The shape and size of the colloidal aggregates are confirmed by optical microscopy and DLS. The aqueous reaction medium, dual role of the catalyst in aqueous media, easy recovery of the catalyst, and high yield make the protocol attractive, sustainable, and economical.