Category: imidazoles-derivatives

Regioselectivity in the Cu(I)-Catalyzed [4 + 2]-Cycloaddition of 2-Nitrosopyridine with Unsymmetrical Dienes was written by Tran, Anh T.;Liu, Peng;Houk, K. N.;Nicholas, Kenneth M.. And the article was included in Journal of Organic Chemistry in 2014.Synthetic Route of C9H8N2O This article mentions the following:

The thermal (uncatalyzed) and Cu(I)-catalyzed reactions of 2-nitrosopyridine (PyrNO) with the dienes 1,3-pentadiene, E,E-2,4-hexadienol, and 1-phenylbutadiene are studied exptl. and computationally. The uncatalyzed reactions of the first two dienes occur with low regioselectivity, while the latter proceeds with complete proximal selectivity. Using the M06/6-311+G(d,p)-SDD method, various concerted transition states for the reactions of 2-nitrosopyridine with (E)-1,3-pentadiene and 1-phenylbutadiene were computed. In quant. agreement with the exptl. findings, (a) no energy difference (0.0 kcal/mol) is found between the most stable transition states, endo-prox-anti and endo-dist-anti, in the pentadiene/PyrNO reaction, leading to nearly equal amounts of prox and dist cycloadducts, and (b) the proximal transition state is strongly favored (by 3.7 kcal/mol) over the distal for the highly selective phenylbutadiene/PyrNO reaction. The regioselectivity of the pentadiene/PyrNO reaction is improved markedly (90:10 dist/prox) when catalyzed by Cu(CH₃CN)₄⁺; (diimine)₂Cu⁺ catalysts increase selectivity for the proximal product (55-65%). Modest effects of the catalyst nature on regioselectivity are observed in the sorbyl alc. and 1-phenylbutadiene reactions. The relative affinity of an equilibrating set of (diimine)₂Cu⁺ complexes for the prox and dist cycloadducts, assessed by ESI-MS, is marginally correlated with the prox/dist product regioselectivity produced by the corresponding catalysts. Transition states in the Cu(CH₃CN)₄⁺– and Cu(diimine)₂⁺-catalyzed reactions are located that account for the observed regioselectivities. Coordination effects on the regioselectivity are derived from FMO orbital interactions and the extent of electron transfer between the Cu center and the coordinated nitroso and diene units. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Synthetic Route of C9H8N2O).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. The solubility of imidazoles in ethers is lower than that in alcohols and decreases with increasing chain length of the ethers . In contrast, the solubility of benzimidazoles in alcohols (C3–C6) is higher than in water and generally decreases with a Imidazole is incorporated into many important biological compounds. The most pervasive is the amino acid histidine, which has an imidazole side-chain. Histidine is present in many proteins and enzymes, e.g. by binding metal cofactors, as seen in hemoglobin.Synthetic Route of C9H8N2O

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Estimation of the solubility with cosolvent composition by combinated of the Williams-Amidon model with quasi virial coefficient was written by Wang, Haiyang;Zhang, Xinwei. And the article was included in Asia-Pacific Journal of Chemical Engineering in 2020.Synthetic Route of C33H34N6O6 This article mentions the following:

A new model that combined the Williams-Amidon model with quasi virial coefficient (WA-QVC) was proposed. Compared with the log-linear model, the modified Wilson model, and the Williams-Amidon model, the WA-QVC model has the highest accuracy to correlate the solubility for cosolvent composition, R²>0.999. For lutelin, it can be seen that the order of R² was WA-QVC>WA>MW>L-L, while the order of root-mean-square deviation was WA-QVC<WA<MW<L-L. Subsequently, the phys. meaning of several model parameters of B₁, X₁, B₂, B₃, and α were discussed and described by the Apelblat model, the exponential model, and the quadratic equation. In addition, the WA-QVC model was tested and verified by solubility data of different solutes in different mixture with higher accuracy, indicating that the WA-QVC model has great application prospect. In the experiment, the researchers used many compounds, for example, 1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5Synthetic Route of C33H34N6O6).

1-(((Cyclohexyloxy)carbonyl)oxy)ethyl 1-((2′-(2H-tetrazol-5-yl)-[1,1′-biphenyl]-4-yl)methyl)-2-ethoxy-1H-benzo[d]imidazole-7-carboxylate (cas: 145040-37-5) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Synthetic Route of C33H34N6O6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

N-Heterocyclic Carbene (NHC)-Stabilized Ru⁰ Nanoparticles: In Situ Generation of an Efficient Transfer Hydrogenation Catalyst was written by Kathuria, Lakshay;Din Reshi, Noor U.;Samuelson, Ashoka G.. And the article was included in Chemistry – A European Journal in 2020.Related Products of 1632-83-3 This article mentions the following:

Tethered and untethered ruthenium half-sandwich complexes I [R = 2,4,6-(CH₃)₃, 4-i-Pr, H, 3-Me, etc.; n = 1, 2] and II were synthesized and characterized spectroscopically. X-ray crystallog. anal. of three untethered I (n = 1, R = 3-OMe; n = 1, R = 4-i-Pr; n = 1, R = 4-NO₂) and two tethered Ru N-heterocyclic carbene (NHC) complexes II (R = 3-OMe, 2,4,6-(CH₃)₃) were also carried out. These RuNHC complexes catalyze transfer hydrogenation of aromatic ketones as acetophenone, 2,3-dihydro-1H-inden-1-one, 1-(furan-2-yl)ethan-1-one, etc. in 2-propanol under reflux, optimally in the presence of (25 mol%) KOH. Under these conditions, the formation of 2-3 nm-sized Ru0 nanoparticles was detected by TEM measurements. A solid-state NMR investigation of the nanoparticles suggested that the NHC ligands were bound to the surface of the Ru nanoparticles (NPs). This base-promoted route to NHC-stabilized ruthenium nanoparticles directly from arene-tethered ruthenium-NHC complexes and from untethered ruthenium-NHC complexes is more convenient than previously known routes to NHC-stabilized Ru nanocatalysts. Similar catalytically active RuNPs were also generated from the reaction of a mixture of [RuCl₂(p-cymene)]₂ and the NHC precursor with KOH in isopropanol under reflux. The transfer hydrogenation catalyzed by these NHC-stabilized RuNPs possess a high turnover number The catalytic efficiency was significantly reduced if nanoparticles were exposed to air or allowed to aggregate and precipitate by cooling the reaction mixtures during the reaction. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Related Products of 1632-83-3).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Related Products of 1632-83-3

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Structural and Photoluminescence Studies of a Europium(III) Tetrakis(β-diketonate) Complex with Tetrabutylammonium, Imidazolium, Pyridinium and Silica-Supported Imidazolium Counterions was written by Bruno, Sofia M.;Ferreira, Rute A. S.;Almeida Paz, Filipe A.;Carlos, Luis D.;Pillinger, Martyn;Ribeiro-Claro, Paulo;Goncalves, Isabel S.. And the article was included in Inorganic Chemistry in 2009.Application In Synthesis of 1-Methyl-3-propylimidazolium Chloride This article mentions the following:

Tetrakis(naphthoyltrifluoroacetonato)lanthanate(III) complexes (Ln = Eu, Gd) containing the cations Bu₄N, [NBu₄]⁺; 1-butyl-3-methylimidazolium, [C₄mim]⁺; and 1-butyl-3-methylpyridinium, [C₄mpyr]⁺, were prepared and structurally characterized by single-crystal x-ray diffraction. The {EuO₈} coordination sphere in [NBu₄][Eu(NTA)₄] is best described as a distorted dodecahedron, where the metal ion is located at the 4-fold inversion axis with only one crystallog. independent NTA residue. In [C₄mim][Eu(NTA)₄] and [C₄mpyr][Gd(NTA)₄], the central Ln³⁺ ions are coordinated by eight O atoms from four distinct β-diketonate ligands, in an overall distorted square-antiprismatic geometry. Besides electrostatic interactions, the crystal packing in all three structures is stabilized by offset π-π interactions involving the naphthyl rings of neighboring complexes (and, for [C₄mim][Eu(NTA)₄] and [C₄mpyr][Gd(NTA)₄], neighboring naphthyl/imidazolium and naphthyl/pyridinium rings) and C-H···π contacts. The photoluminescence properties of the three Eu^III complexes were studied at room temperature and -259° by measuring emission and excitation spectra, ⁵D emission decay curves, and absolute emission quantum yields. Under ligand excitation (λ_ex = 290-395 nm), the quantum yields (room temperature) were in the range 0.72-0.77 for the 1-butyl-3-methylimidazolium salt. An immobilized analog of this complex was prepared by supporting [Eu(NTA)₄]^– on an ordered mesoporous SiO₂ derivatized with 1-propyl-3-methylimidazolium groups. The disappearance of the intra-4f⁶ lines in the excitation spectrum of the supported material indicated an increase in the ligand’s sensitization process of the Eu³⁺ ions, relative to direct intra-4f⁶ excitation. The emission quantum yield measured for the supported material (0.32-0.40, for excitations between 265 and 360 nm) is the highest so far reported for lanthanide-containing ordered mesoporous silicas. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Application In Synthesis of 1-Methyl-3-propylimidazolium Chloride).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) belongs to imidazole derivatives. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. Imidazole has become an important synthon in the development of new drugs. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Application In Synthesis of 1-Methyl-3-propylimidazolium Chloride

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

An efficient method for the preparation of 4(5)-cyanoimidazoles was written by Leone-Bay, Andrea;Glaser, Laurel. And the article was included in Synthetic Communications in 1987.SDS of cas: 26832-08-6 This article mentions the following:

Imidazolecarboxylates I (R¹ = H, alkyl, Ph; R² = H, Br; R³ = H, Me) were amidated to carboxamides II, which were heated with PhP(O)Cl₂ to give III. In the experiment, the researchers used many compounds, for example, 1H-Imidazole-4-carboxamide (cas: 26832-08-6SDS of cas: 26832-08-6).

1H-Imidazole-4-carboxamide (cas: 26832-08-6) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.SDS of cas: 26832-08-6

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Iodine-promoted direct thiolation (selenylation) of imidazole with disulfides (diselenide): A convenient and metal-free protocol for the synthesis of 2-arylthio(seleno)imidazole was written by Yi, Rongnan;Liu, Sen;Gao, Hongxia;Liang, Zhiwu;Xu, Xinhua;Li, Ningbo. And the article was included in Tetrahedron in 2020.Electric Literature of C8H8N2 This article mentions the following:

A convenient and metal-free protocol for the synthesis of 2-arylthio(seleno)imidazoles I (R¹ = Me, Bu, propan-2-yl, tert-butyl; R² = 4-methylphenyl, benzyl, naphthalen-1-yl, etc.; R³ = R⁴ = H; R³R⁴ = -CH=CHCH=CH-; X = S, Se) from imidazoles II and disulfides R²SSR²/diselenides R²SeSeR² was developed through the direct thiolation (selenylation) of imidazoles II promoted by 0.5 equivalent of iodine. This process is scalable and tolerates a wide spectrum of disulfides (diselenides) to deliver products I in high yields. Compared with previous methods, this protocol has the advantages of a simple operation, wide functional group tolerance and good yields, providing an efficient route to 2-arylthio(seleno)imidazoles I, which are key structural scaffolds of many natural products. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Electric Literature of C8H8N2).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. 1H-imidazole is an imidazole tautomer which has the migrating hydrogen at position 1. It is a conjugate base of an imidazolium cation. It is a conjugate acid of an imidazolide. It is a tautomer of a 4H-imidazole. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Electric Literature of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reductive acylation of 4-nitroazoles. Synthesis of N-(4-azolyl)acetamides, N-(4-azolyl)succinimides and N-(4-azolyl)phthalimides was written by Suwinski, Jerzy;Wagner, Pawel. And the article was included in Polish Journal of Applied Chemistry in 2000.Category: imidazoles-derivatives This article mentions the following:

N-Azolylamides have been obtained by the reductive acylation of nitroazoles with acetic, succinic or phthalic anhydrides. N-Azolylsuccinamic and N-azolylphthalamic acids, formed from nitroazoles and the cyclic anhydrides, have been cyclocondensed by treatment with acetic anhydride-sodium acetate mixture to give N-azolylimides. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Category: imidazoles-derivatives).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole also acts as a microtubule destabilizing agents and inhibits topoisomerase and Cytochrome P450 Family 26 Subfamily A Member 1 (CYP26A1) enzymes.Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Influence of 6- or 8-substitution on the antiviral activity of 3-arylalkylthiomethylimidazo[1,2-a]pyridine against human cytomegalovirus (CMV) and varicella-zoster virus (VZV): Part II was written by Veron, Jean-Baptiste;Allouchi, Hassan;Enguehard-Gueiffier, Cecile;Snoeck, Robert;Andrei, Graciela;De Clercq, Erik;Gueiffier, Alain. And the article was included in Bioorganic & Medicinal Chemistry in 2008.SDS of cas: 217435-65-9 This article mentions the following:

The synthesis of original imidazo[1,2-a]pyridines bearing a thioether side chain at the 3 position and diversely substituted on the 6 or 8 position, and their antiviral activities are reported. From the synthesized compounds, the imidazo[1,2-a]pyridines bearing a 5 membered heterocycle (thiophene, furane or pyrrole) in the 6 position or a phenylthio group in the 6 or 8 position (14, 16, 21, 28, 45) were the most potent against human cytomegalovirus (CMV) and varicella-zoster virus (VZV), whereas several other congeners (i.e., 22, 29 and 39), while less potent, were more selective in their inhibitory activity against VZV and CMV. These compounds showed similar activity against thymidine kinase competent (TK⁺) and deficient (TK^–) VZV strains, demonstrating a mechanism of action independent of the viral thymidine kinase. In the experiment, the researchers used many compounds, for example, 6-Bromo-8-methylimidazo[1,2-a]pyridine (cas: 217435-65-9SDS of cas: 217435-65-9).

6-Bromo-8-methylimidazo[1,2-a]pyridine (cas: 217435-65-9) belongs to imidazole derivatives. Imidazole derivatives generally have good solubility in protic solvents. Simple imidazole derivatives, such as 1H-imidazole, 2-methyl-1H-imidazole, and 1,2-dimethylimidazole, have very high solubility in water. Imidazole based anticancer drug find applications in cancer chemotherapy. It is used as buffer component for purification of the histidine tagged recombinant proteins in immobilized metal-affinity chromatography (IMAC).SDS of cas: 217435-65-9

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Controlled fragrance delivery in functionalized ionic liquid-enzyme systems was written by Blesic, Marijana;Nimal Gunaratne, H. Q.;Nockemann, Peter;McCarron, Philip;Seddon, Kenneth R.. And the article was included in RSC Advances in 2013.Application of 21252-69-7 This article mentions the following:

It is often believed that both ionic liquids and surfactants generally behave as non-specific denaturants of proteins. In this study, it is shown that amphiphilic ionic liquids bearing a long alkyl chain and a target mol., where the target mol. is appended via a carboxylic ester functionality, can represent super-substrates that enable the catalytic activity of an enzyme, even at high concentrations in solution Menthol was chosen as the target mol. for slow and controlled fragrance delivery, and it was found that the rate of the menthol release can be controlled by the chem. structure of the ionic liquid At a more fundamental level, this study offers an insight into the complex hydrophobic, electrostatic, and hydrogen bond interactions between the enzyme and substrate. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Application of 21252-69-7).

1-Octyl-1H-imidazole (cas: 21252-69-7) belongs to imidazole derivatives. Many natural products, especially alkaloids, contain the imidazole ring. These imidazoles share the 1,3-C3N2 ring but feature varied substituents. The pharmacophore of imidazole exists in bioactive compounds including amino acids, plant growth regulators and therapeutic agents.n increase of the alkyl chain length of the alcohols. Application of 21252-69-7

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

N-Heterocyclic Carbene-Transition Metal Complexes: Spectroscopic and Crystallographic Analyses of π-Back-bonding Interactions was written by Khramov, Dimitri M.;Lynch, Vincent M.;Bielawski, Christopher W.. And the article was included in Organometallics in 2007.Electric Literature of C4H5N3O2 This article mentions the following:

The ability of N-heterocyclic carbenes (NHCs) to participate in π-back-bonding interactions was evaluated in a range of transition metal complexes. Rh chloride complexes containing a systematic series of various 1,3-dimethyl-4,5-disubstituted-imidazol-2-ylidenes and either 1,5-cyclooctadiene (cod) or two CO ligands were synthesized (i.e., (NHC)RhCl(cod) and (NHC)RhCl(CO)₂, resp.; NHC = C₃N₂Me₂-1,3-R₂-4,5 (R = H, Cl, CN)) and studied using ¹H NMR and IR spectroscopies. In the former series, the ¹H NMR chem. shifts of the signals attributable to the olefin trans to the NHC ligand shift downfield by up to 0.17 ppm as the π-acidity of the substituents on the 4,5-positions increased (i.e., H â†?Cl â†?CN). Similarly, in the latter series, the IR stretching frequencies of the carbonyl groups trans to the NHC ligands increase by 11 ± 0.5 cm^-1 as π-acidity increased over the same series. Using the nitrile group as a diagnostic handle, the CN stretching frequency of (1,3-dimethyl-4,5-dicyanoimidazol-2-ylidene)(cod)RhCl is 4 ± 0.5 cm^-1 > (1,3-dimethyl-4,5-dicyanoimidazol-2-ylidene)(CO)₂RhCl, a more π-acidic analog. X-ray anal. of the aforementioned series of (NHC)(cod)RhCl complexes indicated changes in N-C_carbene bond lengths that were consistent with greater π-donation from complexes containing 4,5-dihydroimidazol-2-ylidene relative to their 4,5-dicyano analogs. Collectively, these results suggest not only that imidazol-2-ylidenes are capable of π-back-bonding but that this interaction may be tuned by changing the π-acidity of the substituents on the imidazole ring. In the experiment, the researchers used many compounds, for example, 1-Methyl-4-nitroimidazole (cas: 3034-41-1Electric Literature of C4H5N3O2).

1-Methyl-4-nitroimidazole (cas: 3034-41-1) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. Imidazole has been usedin the lysis, wash and elution buffer for the purification of histidine tagged Sonic Hedgehog(shh-N) protein, in elution buffer in stepwise gradient for the purification of histidine tagged aldo keto reductases using nickel affinity chromatography, as a component of homogenization buffer for the purification of phagosomal compartments from dendritic cells.Electric Literature of C4H5N3O2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem