492-73-9

Usage

Uses

Used in Analytical Chemistry:
Di-2-pyridylglyoxal is used as a chelating agent for the detection and quantification of metal ions, leveraging its selective binding capabilities to ensure accurate measurements and analysis.
Used in Biochemistry:
In biochemistry, Di-2-pyridylglyoxal is utilized as a reagent to study metal ion-dependent biological processes, providing insights into the roles and interactions of metal ions within biological systems.
Used in Sensor Development:
Di-2-pyridylglyoxal is employed in the development of metal ion-based sensors, capitalizing on its chelating properties to create sensitive and selective detection mechanisms for various metal ions.
Used in Medicinal Chemistry:
Di-2-pyridylglyoxal is used as a component in the research and development of metal-based anticancer drugs, exploring its potential to contribute to novel therapeutic approaches against cancer.
Used in Pharmaceutical Industry:
Within the pharmaceutical industry, Di-2-pyridylglyoxal is used as a key compound in the formulation and synthesis of metal-based drugs, particularly those with anticancer properties, due to its ability to chelate metal ions effectively.

Upstream product

• 1121-60-4 pyridine-2-carbaldehyde 
• 1141-06-6 2-hydroxy-1,2-di-2-pyridylethanone 
• 1115-15-7 divinyl sulfoxide 
• 134296-07-4 6-formyl-2,2'-bipyridine 
• 586-98-1 2-Hydroxymethylpyridine 
• 109-06-8 α-picoline 
• 41661-47-6 piperidin-4-one 
• 3891-65-4 1,2-di(pyridin-2-yl)ethene-1,2-diol 

Downstream Products

• 25005-95-2 2,3-bis(2'-pyridyl)-5,6-dihydropyrazine 
• 19437-26-4 2,2'-dipyridyl ketone 
• 1141-06-6 2-hydroxy-1,2-di-2-pyridylethanone 
• 69466-57-5 3-methylsulphanyl-5,6-di-pyridin-2-yl-[1,2,4]triazine 
• 153179-95-4 5-trifluoromethyl-6-phenylsulfonyl-1,2-di(2-pyridyl)-3,4-diazahexa-2,4-dien-1-one 
• 6627-38-9 6,7-dimethyl-2,3-di(2-pyridyl)quinoxaline 
• 98-98-6 2-Picolinic acid 
• 111531-11-4 pyridine-2-carboxylic acid-(2-oxo-1,2-di-[2]pyridyl-ethylamide) 
• 19793-82-9 1,2-di(2-pyridyl)-1,2-ethanediol 
• 1141-05-5 1,2-di-2-pyridinyl-1,2-ethanediol 

Relevant academic research and scientific papers

Oxidation of benzoin to benzil using Burgess Reagent

Synthetic utility of Burgess Reagent for the mild and efficient oxidation of benzoins to benzils is discussed.

Palladium(II)complexes of ambidentate and potentially cyclometalating 5-aryl-3-(2′-pyridyl)-1,2,4-triazine ligands

The 5-aryl-3-(2′-pyridiyl)-1,2,4-triazine ligands under study [5-phenyl-(PyTZPh)L1 5-(3-methoxyphenyl)-(PyTZ3Me-OPh)L2 5-(4-methoxyphenyl)-(PyTZ4MeOPh)L3 5-(4-trifluoromethylphenyl)-(PyTZ4CF3Ph)L4 5-(4-fluorophenyl)-(PyTZ4FPh)L5 and tris-3,5,6-(2′-pyridyl)-1,2,4-triazine (Py3TZ)L6] react with [(COD)PdCl2] (COD = 1,5-cyclooctadiento form complexes [(L1-6)PdCl2] with N,N bidentate binding ligands, also including the potentially N,N,N tridentate ligand L6. This was concluded from an in-depth NMR spectroscopic study of the new complexes and from comparison with Pd-terpy complexes [(R′ terpy)PdCl]Cl [R′terpy = 4′-R′-2,2′:6′,2′′-terpyridine R′ = H or SMe], showing definite tridentate N,N,N coordination, and with the Pd-bpy complexes [(bpy)Pd(Mes)Cl] and [(bpy)PdCl2], show-ing definite bidentate N,N binding. The new ligands and complexes were fully characterised by multinuclear NMR spectroscopy, IR spectroscopy and mass spectrometry. No evidence for the parent triazine complexes is observed in EI-MS instead, cyclometalated complexes (HCl eliminatiowere detected in all cases. TDA/TG experiments support this assumption. Attempts to prepare the cyclometalated derivatives as substances failed, in line with the unfavourable binding mode. Detailed electrochemical measurements reveal ligand-centred reductions at very moderate potentials, in line with UV/Vis absorption spectroscopy and DFT calculations, revealing very low-lying triazine-centred LUMOs. Results from cyclic voltammetry also support the composition of [(Py3TZ)PdCl2].

CO2-assisted synthesis of non-symmetric α-diketones directly from aldehydes: Via C-C bond formation

CO2-assisted various symmetric and non-symmetric α-diketones have been synthesized directly from the corresponding aldehydes using transition metal-free catalysts. This method can even be applied to synthesize pharmaceuticals directly from aldehydes. The crucial role of CO2 has been investigated in detail and the mechanism is proposed on the basis of experiments and DFT calculations.

Dendrimer-like core cross-linked micelle stabilized ultra-small gold nanoclusters as a robust catalyst for aerobic oxidation of α-hydroxy ketones in water

As one of the most general and promising stabilizers, dendrimers have been widely used to prepare ultra-small gold nanoclusters. However, the complex synthesis of dendrimers hinders the further application of protected nanoclusters. Here we report a facile strategy to prepare an alternative material via core cross-linking of self-assembled micelles. The resulting dendrimer-like core cross-linked micelles (DCCMs) retain the main characteristics of dendrimers and avoid complex chemical synthesis. As expected, the DCCMs could easily encapsulate gold nanoparticles within their cores. The ultra-small clusters of Au5 were prepared without the participation of external reductants. Importantly, the DCCM stabilized noble gold clusters furnish excellent catalytic activity and perfect reusability for aerobic oxidation of α-hydroxy ketones in water. Only in open air the oxidation could be repeated up to 48 times with negligible turn-over frequency change. The total turnover number (TON) of the reaction reached unexpectedly >48 000, the highest TON for metal catalysed oxidation of hydroxy ketones so far. The further mechanism study hints that the carboxylic group of substrates might be involved in the catalytic process. The simple catalyst preparation, the environmentally benign reaction conditions, and the excellent catalytic performance and durability make the novel DCCM protected gold nanocluster a green catalyst.

PTSA-catalyzed one-pot synthesis of quinoxalines using DMSO as the oxidant

An efficient p-toluene sulfonic acid–catalyzed, one-pot, two-step oxidative system for cyclization of o-diaminobenzene with 1,2-diaryl-2-hydroxyethanone to quinoxalines was described. A nontoxic, readily available oxidant, dimethylsulfoxide (DMSO), was applied in this process. A broad range of substrates was applied to this method, and target compounds were obtained with good yields.

An efficient iodine-DMSO catalyzed synthesis of quinoxaline derivatives

An efficient iodine-DMSO catalyzed system for the synthesis of quinoxaline derivatives was developed. The construction of this quinoxaline system went through a one-pot oxidation/cyclization process. The reaction afforded a variety of products in good to excellent yields. This methodology has potential applications in the synthesis of biologically and medicinally relevant compounds.

Deformative transition of the menschutkin reaction and helical atropisomers in a congested polyheterocyclic system

A 4,7-phenanthroline polycyclic 1A designed for probing the limits of the Menschutkin reaction was synthesized in a six-step sequence. The rotational barrier of the phenyl ring nearby the N-methyl group in rac-2A was estimated to be 18.1 kcal/mol from VT-NMR experiments, making them a new type of helical atropisomer. The methylation rate constants of 9 and 1A with MeI was found to be 2.22 × 10-4 and 9.62 × 10-6 s-1 mol-1 L, respectively; thus, the formation rate of (P/M)-2A is one of the slowest rates ever reported for a Menschutkin reaction. The N-methyl protons in (P/M)-2A exhibit a significant upfield shift (Δδ 1.0 ppm) in its 1H NMR, compared to those without a nearby phenyl, indicating a strong CH-π interaction is involved. Conformational flexibility in dipyridylethene 9 is clearly shown by its complexation with BH3 to form helical atropisomers (P,P/M,M)-10. The pKa values of the conjugate acids of 1A and 9 in acetonitrile were determined to be 4.65 and 5.07, respectively, which are much smaller compared to that of pyridine 14a (pKa = 12.33), implying that the basicity, nucleophilicity, and amine alkylation rates of 1A and 9 are markedly decreased by the severe steric hindrance of the flanking phenyl rings in the polyheterocycles.

Evaluation and Development of Practical Routes to an Enantiomerically Pure C 2-Symmetric Diamine Building Block

Several routes to an enantiomerically pure C2-symmetric diamine were evaluated and modified to scalable methods. A Zn/Me3SiCl- mediated reductive coupling of an imine was found to be superior to the other methods investigated, allowing us to safely prepare the enantiomerically pure diamine also on a large scale. One key step in this method was a highly efficient resolution of a stereoisomeric mixture of the diamine through salt formation with (-)-dibenzoyl-l-tartaric acid. The enantiomerically pure C 2-symmetric diamine obtained was further used as a key building block for the synthesis of potent Kv1.5 channel blockers.

CuI-catalyzed and air promoted oxidative cyclization for one-pot synthesis of polyarylated oxazoles

A facile CuI-catalyzed and air promoted oxidative cyclization was developed for the synthesis of polyarylated oxazoles. By virtue of this method, a variety of arylated oxazoles could be easily synthesized from readily available starting materials at room temperature in air. The Royal Society of Chemistry 2013.

CaO-catalyzed aerobic oxidation of α-hydroxy ketones: Application to one-pot synthesis of quinoxaline derivatives

The aerobic oxidation of α-hydroxy ketones into α-diketones catalyzed by CaO is compared with the same reaction catalyzed by other metal oxides. The catalytic activities of the various metal oxides were proportional to their surface basicities. The direct conversion of α-hydroxy ketones into quinoxalines via CaO-catalyzed aerobic oxidation followed by in situ reaction with 1,2-diaminoaromatics is also achieved. Various types of quinoxalines were synthesized in the presence of the CaO catalyst and molecular oxygen. It was also found that the CaO catalyst was reusable without any loss of its catalytic activity.