6581-76-6

Upstream product

• 5118-57-0 methylenebis-2,2'-(1,2,3,4-tetrahydronaphthalen-1-one) 
• 631-61-8 ammonium acetate 
• 50-00-0 formaldehyd 
• 529-34-0 3,4-dihydronaphthalene-1(2H)-one 
• 28353-74-4 3,4-dihydronaphthalen-1(2H)-one O-acetyl oxime 
• 68-12-2 N,N-dimethyl-formamide 
• 124-38-9 carbon dioxide 
• 4637-24-5 N,N-dimethyl-formamide dimethyl acetal 
• 16712-16-6 ammonium formate 
• 5166-71-2 ±-2-dimethylaminomethyl-3,4-dihydronaphthalen-1(2H)-one hydrochloride 
• 3262-03-1 1-chloro-2-formyl-3,4-dihydronaphthalene 
• 67-68-5 dimethyl sulfoxide 

Downstream Products

• 224-53-3 dibenz[c,h]acridine 

Relevant academic research and scientific papers

Aqueous CO2fixation: construction of pyridine skeletons in cooperation with ammonium cations

A simple and green method is explored for the synthesis of fused pyridines by [2 + 2 + 1 + 1] the cycloaddition of ketones with an ammonium cation under a CO2atmosphere. The reactions employed ammonium cation as a nitrogen source and CO2gas as a carbon source in an aqueous solution. Monoethanolamine (MEA) was used as an additive to increase the solubility of CO2in an aqueous solution. The scope and versatility of the method are demonstrated with 38 examples. Products are found to be photosensitive and show potential applications as organic optoelectronic materials. A selectfluor-promoted reaction mechanism is proposed based on the experimental studies. Our work is superior as it is a metal-free system, uses CO2as a carbon source and MEA as an additive in aqueous synthesis.

Preparation method and application of fused ring pyridine compound and derivative thereof

The invention discloses a preparation method of a fused ring pyridine compound. The preparation method comprises the following steps: in an atmosphere containing carbon dioxide, taking a fused ring ketone compound and a nitrogen source as raw materials, and reacting in a water phase in the presence of an oxidizing agent, an alkali and an alcohol amine compound to obtain a product containing the fused ring pyridine compound. According to the method, the condensed ring pyridine compound is synthesized in the water phase in an atmosphere containing carbon dioxide gas by taking the fused ring ketone compound as the raw material and ammonium ions as a nitrogen source under the combined action of the oxidizing agent, the alkali and t ahelcohol amine compound, and the method is low in cost, green, environment-friendly and easy to operate.

Indium(iii)-catalyzed solvent-free multicomponent [2 + 2 + 1 + 1]-annulation to polycyclic functionalized fused pyridines as potential optical chemosensors

An In(iii)-catalyzed solvent-free one-pot [2 + 2 + 1 + 1]-annulation for the construction of highly fused polycyclic functionalized pyridines as a novel green approach is described. This unique reaction yields a wide range of polycyclic products bearing dihydrobenzoquinoline, azafluorene, azafluorenone, pyridocoumarin, and benzocycloheptapyridine frameworks. The synthesized compounds exhibit excellent photophysical properties as new fluorophores and metal ion chemosensors.

Cyclometalated pt complexes of cnc pincer ligands: Luminescence and cytotoxic evaluation

In the framework of our attempts to develop cyclometalated Pt(II) complexes toward bifunctional targeting inhibitors or agents for photodynamic therapy, diagnostics, and bioimaging, a series of bis-cyclometalated Pt(II) complexes [Pt(CNC)(L)] (L = DMSO, MeCN) containing various (CNC)2- ligands based on 2,6-diphenylpyridine were synthesized and characterized analytically and spectroscopically, focusing on their electrochemical, luminescence, and antiproliferative properties. Electrochemical experiments and UV-vis absorption spectroscopy suggest ligand-centered LUMOs and metal-centered HOMOs in line with DFT calculations. Extension of the ancillary phenyl to naphthyl cores and a central 4-phenylpyridine group instead of pyridine results in bathochromic shifts of the long-wavelength absorption bands ranging from 420 to 440 nm, with the latter shift being more pronounced. The complexes of the fused CNC heterocyclic systems dba (H2dba = dibenzo[c,h]acridine), db(ph)a (H2db(ph)a = 7-phenyldibenzo[c,h]acridine), and bzqph (HbzqphH = 2-phenylbenzo[h]quinoline) absorb far more red-shifted in the range 500-530 nm. All complexes show reversible first electrochemical reductions and irreversible oxidations with an electrochemical gap of about 3 V, roughly in line with the absorption energies. While the 2,6-diphenylpyridine complexes [Pt(CNC)(DMSO)] show no luminescence at ambient temperature in solution, the fused dba, db(ph)a, and bzqph derivatives are efficient triplet emitters at ambient temperature with emission wavelengths in the region 575-600 nm and quantum yields ranging from 7 to 23%. Vibrationally resolved emission spectra calculated in the framework of DFT faithfully reproduce the experimental data. TD-DFT calculations at the excited-state T1 geometry reveal intraligand π-π*/MLCT character of the emission for all three investigated complexes. Antiproliferative tests on selected complexes gave very different toxicities, ranging from lower than 1 μM to virtually nontoxic. The data allowed drawing some structure-activity relationships (SAR), even though variations in solubility could also significantly account for the different toxicities.

An Efficient Synthesis of Polysubstituted Pyridines via C sp 3 -H Oxidation and C-S Cleavage of Dimethyl Sulfoxide

An expedient cleavage of the C-S bond of dimethyl sulfoxide (DMSO) has been developed for the preparation of substituted pyridines from ketones. In this transformation, the co-product formic acid was formed from ammonium formate, which acted as an important catalyst for the reaction. Notably, this transformation exhibited a broad substrate scope towards a wide variety of different ketones to give the corresponding substituted pyridines in high yields. Mechanistic studies suggested that dimethyl sulfoxide delivered a methylene fragment, which was subsequently captured in situ to give a pyridine.

Ruthenium-catalyzed cyclization of ketoxime acetates with DMF for synthesis of symmetrical pyridines

A novel ruthenium-catalyzed cyclization of ketoxime carboxylates with N,N-dimethylformamide (DMF) for the synthesis of tetrasubstituted symmetrical pyridines has been developed. A methyl carbon on DMF performed as a source of a one carbon synthon. And NaHSO3 plays a role in the reaction.

DPTA-catalyzed one-pot regioselective synthesis of polysubstituted pyridines and 1,4-dihydropyridines

With diphenylammonium triflate (DPAT) as a catalyst, the highly substituted pyridines and dihydropyridines were prepared under solvent-free conditions from aldehydes, ketones, and amines via a one-pot multi-component reaction. The advantages of this protocol include excellent yields, environmentally benign source of nitrogen, mild reaction conditions, and simple manipulation. Different source of nitrogen like urea, thiourea, inorganic ammonium salts, and organic amines were studied. In addition, a novel way was developed for the conversion of primary aliphatic amines into alcohols.

A New Method for the Synthesis of Ring-Fused Pyridines

An easy, one-step synthesis of pyridine derivatives 4 has been developed by condensation of enamines with iminium salts (Method A).This method could also be modified to yield unsymmetrically substituted derivatives (condensation of Mannich bases with ketones; Method B).