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Upstream product

• 19437-26-4 2,2'-dipyridyl ketone 
• 100-46-9 benzylamine 
• 100-52-7 benzaldehyde 

Relevant academic research and scientific papers

Highly efficient and direct heterocyclization of dipyridyl ketone to N,N-bidentate ligands

(Chemical Equation Presented) Reaction of various aromatic aldehydes with 2,2′-dipyridyl ketone and ammonium acetate in hot acetic acid provides ready access to a series of substituted 1-pyridylimidazo[1,5-a]pyridines, a class of ligands possessing an N,N-bidentate feature, in good yields.

Synthesis and characterization of new Pd(ii) and Pt(ii) complexes with 3-substituted 1-(2-pyridyl)imidazo[1,5-a]pyridine ligands

Several palladium(ii) and platinum(ii) complexes (1-20) of general formula [M(Ln)(X)(Y)] [M = Pd, X = Y = Cl (1-Cl-4-Cl), X = Y = OAc (1-OAc-4-OAc); M = Pt: X = Y = Cl (5-8); M = Pd, X = Cl, Y = CH3(9-12); M = Pt, X = Cl, Y = CH3(13-16) or X = Y = CH3(17-20);n= 1-4] have been synthesized by reaction of different Pd(ii) and Pt(ii) derivatives with various 3-substituted 1-(2-pyridyl)-imidazo[1,5-a]pyridines;i.e.Ln= 1-(2-pyridyl)-3-arylimidazo[1,5-a]pyridine (aryl = Phenyl,L1; 2-o-Tolyl,L2; Mesityl,L3) and 1-(2-pyridyl)-3-benzylimidazo[1,5-a]pyridine (L4). Detailed spectroscopic investigation (including IR, mono- and bi-dimensional1H NMR) and elemental analysis has been performed for all these species, allowing their complete characterization.Lnact asN,N-bidentate ligands and coordinate the metal centers in a chelate fashion through the pyridyl (Npy) and the pyridine-like nitrogen atom of the imidazo[1,5-a]pyridine group (Nim). The X-ray structural analysis performed on two of Pd(ii) and three Pt(ii) complexes, namely [Pd(L2)(CH3)Cl] (10), [Pd(L3)(CH3)Cl] (11) and [Pt(L1)Cl2] (5), [Pt(L4)Cl2] (8), [Pt(L2)(CH3)Cl] (14) confirmed the spectroscopic and analytical data. Finally DFT studies unveiled the structural reasons behind the inertia of the synthesised compounds toward metalation, identified as the higher angle steric strain in comparison with the analogous bipyridine complexes.

Ionic liquid promoted facile one-pot synthesis of 1-pyridylimidazo[1,5-a] pyridines from dipyridylketone and aryl aldehydes

A highly efficient one-pot methodology has been developed to synthesize a class of substituted 1-pyridylimidazo[1,5-a]pyridines, using Bronsted acidic ionic liquid 1-butylimidazolium tetrafluoroborate, [Hbim]BF4 in excellent isolated yields in

Coordination geometry-induced optical imaging of L-cysteine in cancer cells using imidazopyridine-based copper(ii) complexes

Overexpression of cysteine cathepsins proteases has been documented in a wide variety of cancers, and enhances the l-cysteine concentration in tumor cells. We report the synthesis and characterization of copper(ii) complexes [Cu(L1)2(H2/s

Versatile Luminescent Europium(III)-β-Diketonate-imidazo-bipyridyl Complexes Intended for White LEDs: A Detailed Photophysical and Theoretical Study

Three ancillary ligands based on imidazo-bipyridyl with phenyl (Ph), naphthyl (Np), and triphenylamine (TPA) substitution were synthesized and secondhand to formulate the consistent europium(III) ternary complexes using thenoyltrifluoroacetone as an anionic ligand. The complete investigation of spectroscopic, photophysical, and electrochemical properties was carried out. The attained results for all the ancillary ligands and their corresponding Eu complexes were compared with one another. All the Eu complexes reveal a broad excitation band ranging from the near-UV to blue region, along with high intense emission and apposite color purity. To further understand the ligand-to-metal energy transfer (ET) process, the geometry of the ligand was optimized and the energy level location (singlet and triplet) was calculated by using DFT and TD-DFT calculations. On the basis of the theoretical calculation, the ET mechanism was proposed. From PL emission spectra in the solid state, complete ET occurs from Ph, Np based ancillary ligands to the Eu3+ ion, which yields a pure red emission, whereas the TPA functionalized based Eu complex shows incomplete ET. Fortunately, white emission was observed in the TPA based Eu complex in the solid state. The white LED was fabricated by using a white emitting complex integrated with 395 nm emitted LED (InGaN) chips under 20 mA forward-bias current. The excitation source from LED was fully observed by the complex shown for 3Eu and showed yellowish emission in different concentrations (the similar observation also reflected in solid). However, in the case of 1Eu and 2Eu complexes, they showed close to white emission. The Commission International de I'Eclairage (CIE) chromaticity coordinates are close to the National Television Standard Committee standard value for white emission, and in addition, the complex 3Eu coated with the blue LED chip (460 nm) by PMMA (1:10) showed bright white emission with CIE x, y values of 0.30, 0.33, respectively.

Blue fluorescent zinc(II) complexes based on tunable imidazo[1,5-a]pyridines

Herein, we investigate the photophysical features of new zinc(II) chlorido complexes containing fluorescent 1,3-substituted imidazo[1,5-a]pyridines as ligands. The derivatives introduce electron-donating or electron-withdrawing moieties in position 3 on the ligand skeleton. The obtained compounds have been characterized with different spectroscopic techniques, their structure has been defined by single-crystal X-ray diffraction and mass spectrometry and their optical properties have been discussed in relation to the chemical structure. The comparison between the emission spectra of the free ligands and of the corresponding zinc(II) chlorido complexes shows an intense hypsochromic shift, due to the modification of the ligands conformation upon metal coordination, and a significant increase of the quantum yield after complexation.

Synthesis of imidazo[1,5-a] pyridines via I2-mediated sp3 C-H amination

A transition-metal-free sp3 C-H amination reaction has been established for imidazo[1,5-a]pyridine synthesis employing molecular iodine from 2-pyridyl ketones and alkylamines. In the presence of sodium acetate (NaOAc), the I2-mediate

Synthesis, structures, and DNA and protein binding of ruthenium(ii)-p-cymene complexes of substituted pyridylimidazo[1,5-a]pyridine: enhanced cytotoxicity of complexes of ligands appended with a carbazole moiety

A series of organometallic Ru(ii)-arene complexes of the type [(η6-p-cymene)Ru(L)Cl](BF4) 1-6, where L is 3-phenyl-1-pyridin-2-yl-imidazo[1,5-a]pyridine (L1), dimethyl-[4-(1-pyridin-2-yl-imidazo[1,5-a]pyridin-3-yl)phenyl]-amine (L2), diphenyl-[4-(1-pyridin-2-yl-imidazo[1,5-a]pyridin-3-yl)phenyl]amine (L3), 9-[4-(1-pyridin-2-yl-imidazo-[1,5-a]pyridin-3-yl)-phenyl]-9H-carbazole (L4), 9-ethyl-3-(1-pyridin-2-yl-imidazo-[1,5-a]pyridin-3-yl)-9H-carbazole (L5), and 10-ethyl-3-(1-pyridin-2-yl-imidazo[1,5-a]pyridin-3-yl)-10H-phenothiazine (L6), has been isolated and characterised by elemental analysis, ESI-MS, NMR and cyclic voltammetry. The photophysical properties of the complexes have been studied by electronic absorption and emission spectral techniques. All the ligands exhibit tuneable photoluminescence behaviour with the emission maximum spanning through the visible region (475-670 nm) in dichloromethane while all the complexes are emissive in acetonitrile. The single crystal X-ray structures of 2, 3 and 4 reveal that the complexes have a “piano stool” coordination geometry, comprising one π-bonded arene centroid, two σ-bonded nitrogen atoms from the chelating ligand and one Cl- ion. From DNA induced EthBr emission quenching experiments the apparent DNA binding constants of the complexes (Kapp) have been evaluated, which follows the order, 2 (1.3) 5 M-1). This trend reveals the role of ligand hydrophobicity on the DNA binding ability of complexes, the non-planar phenothiazine ring (6) and the specific interactions the planar carbazole chromophore (4, 5) make with DNA. The value of Ksv obtained as the slope of the linear plot of F0/F vs. [complex] follows the order 1 (3.1) -1), which supports the inferences from DNA binding experiments. All the complexes, except, 1 and 2 (>100 μM), exhibit in vitro cytotoxicity against A549 small lung cancer cell lines higher than cisplatin (～69 μM), as revealed by both MTT (11.8-18.1 μM) and crystal violet staining (12.7-23.5 μM) assays, which is in agreement with their DNA and BSA binding affinity. Also, the complexes 3-6 cause higher cell death mainly through the apoptotic mode, as revealed by the observation of a higher percentage of apoptotic cells in AO/EB (36-43%) and Annexin V-Cy3 (36-45%) stained cancer cells.

Scandium(III) triflate-catalyzed efficient synthesis of substituted 1-pyridylimidazo-[1,5-a]-pyridines

An efficient synthesis of substituted 1-pyridylimidazo-[1,5-a]-pyridines has been accomplished using scandium(III) triflate as catalyst under mild conditions in excellent yields.

SYNTHESIS OF 1,3-DISUBSTITUTED IMIDAZOPYRIDINES.

Facile syntheses of 1,3-disubstituted imidazopyridines have been effected by treatment of ketimines derived from di-2-pyridyl ketone with LDA and benzophenone, reactions of benzyl amine with di-2-pyridyl ketone in boron trifluoride etherate, and re