Category: imidazoles-derivatives

Akana, Jennifer A.; Bhattacharyya, Koyel X.; Mueller, Peter; Sadighi, Joseph P. published an article in Journal of the American Chemical Society. The title of the article was 《Reversible C-F Bond Formation and the Au-Catalyzed Hydrofluorination of Alkynes》.Computed Properties of C27H38AuClN2 The author mentioned the following in the article:

The gold(I) fluoride complex [(SIPr)AuF] [SIPr = 1,3-bis(2,6-diisopropylphenyl)imidazolin-2-ylidene] reacts reversibly with 3-hexyne to form a (β-fluorovinyl)gold(I) species. The more stable fluorovinyl complex trans-{(SIPr)Au[(Ph)C:C(F)CH3]}, formed by addition of [(SIPr)AuF] across 1-phenyl-1-propyne, has been characterized crystallog. Both the protonolysis of a (fluorovinyl)gold complex and the reaction of a cationic (alkyne)gold(I) complex with the mild HF source Et3N•3HF result in fluoroalkene formation. Electrophilic gold(I) complexes, supported by N-heterocyclic carbene ligands and generated in situ, catalyze the trans-hydrofluorination of internal alkynes at room temperature This catalysis represents a new, selective, and potentially versatile method for the synthesis of fluoroalkenes. In addition to this study using Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I), there are many other studies that have used Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2Computed Properties of C27H38AuClN2) was used in this study.

Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2) belongs to imidazoles.Imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies.
Computed Properties of C27H38AuClN2 However, the application of imidazoles is not limited to the field of peptides and peptidomimetics.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Reference of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)On October 16, 2013 ,《Gold-Mediated Expulsion of Dinitrogen from Organic Azides》 was published in Journal of the American Chemical Society. The article was written by Dash, Chandrakanta; Yousufuddin, Muhammed; Cundari, Thomas R.; Dias, H. V. Rasika. The article contains the following contents:

Organoazides and their nitrogen expulsion chem. have attracted the attention of many scientists because they serve as a useful source of nitrene fragments and interesting nitrene rearrangement products. Gold-mediated reactions are also of significant current interest. This manuscript describes several important discoveries based at the intersection of these fields. In particular, the authors report the first isolable gold organoazides ([(SIPr)-AuN-(1-Ad)-NN][SbF6], [(SIPr)-AuN-(2-Ad)-NN][SbF6] and [(SIPr)-AuN-(Cy)-NN][SbF6]; SIPr = a N-heterocyclic carbene; 1-AdNNN = 1-azido-adamantane; 2-AdNNN = 2-azidoadamantane; CyNNN = azidocyclohexane), and their gold-mediated nitrogen expulsion chem., and the isolation of formal nitrene rearrangement products of 1-AdN, 2-AdN and CyN (including the elusive 4-azahomoadamant-3-ene) as their gold complexes. The authors have also performed a computational study to understand and explain the observed structure of gold-coordinated 1-AdNNN and 2-AdNNN and their nitrogen elimination pathways, which implies that the conversion of the organoazide complex to the imine is a concerted process without a nitrene/nitrenoid intermediate. Kinetic studies of [(SIPr)-AuN-(2-Ad)-NN][SbF6] from 30 to 50 °C indicate that nitrogen elimination is a first-order process. The exptl. determined activation parameters are in good agreement with the calculated values. The experimental part of the paper was very detailed, including the reaction process of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2Reference of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I))

Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I)(cas: 852445-84-2) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Reference of Chloro{1,3-bis[2,6-bis(1-methylethyl)phenyl]-4,5-dihydroimidazol-2-ylidene}gold(I) Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

HPLC of Formula: 258278-25-0On May 8, 2019 ,《Nickel-Catalyzed Decarboxylation of Aryl Carbamates for Converting Phenols into Aromatic Amines》 appeared in Journal of the American Chemical Society. The author of the article were Nishizawa, Akihiro; Takahira, Tsuyoshi; Yasui, Kosuke; Fujimoto, Hayato; Iwai, Tomohiro; Sawamura, Masaya; Chatani, Naoto; Tobisu, Mamoru. The article conveys some information:

Herein, we describe a new catalytic approach to accessing aromatic amines from an abundant feedstock, namely phenols. The most reliable catalytic method for converting phenols to aromatic amines uses an activating group, such as a trifluoromethane sulfonyl group. However, this activating group is eliminated as a leaving group during the amination process, resulting in significant waste. Our nickel-catalyzed decarboxylation reaction of aryl carbamates forms aromatic amines with carbon dioxide as the only byproduct. As this amination proceeds in the absence of free amines, a range of functionalities, including a formyl group, are compatible. A bisphosphine ligand immobilized on a polystyrene support (PS-DPPBz) is key to the success of this reaction, generating a catalytic species that is significantly more active than simple nonsupported variants. The results came from multiple reactions, including the reaction of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0HPLC of Formula: 258278-25-0)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.HPLC of Formula: 258278-25-0In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Electric Literature of C10H12N2OOn October 20, 2010 ,《Tetra butyl ammonium chloride catalyzed synthesis of substituted benzimidazoles under microwave conditions》 was published in Journal of the Korean Chemical Society. The article was written by Karuvalam, Ranjith. P.; Siji, M.; Divia., N.; Haridas, Karickal. R.. The article contains the following contents:

Tetrabutylammonium chloride (10 mol%) was a useful catalyst for the synthesis of substituted benzimidazoles from o-phenylenediamines with benzoic acids. The method was simple, convenient and the product was isolated with good yield. In addition to this study using 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol, there are many other studies that have used 3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9Electric Literature of C10H12N2O) was used in this study.

3-(1H-Benzo[d]imidazol-2-yl)propan-1-ol(cas: 2403-66-9) belongs to imidazoles.Imidazole rings are also present in imidazole ring alkaloids, which are potential therapeutics for thrombosis, cancer and inflammatory diseases.Electric Literature of C10H12N2O Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Polyethylene Aerogels with Combined Physical and Chemical Crosslinking: Improved Mechanical Resilience and Shape-Memory Properties》 was published in Angewandte Chemie, International Edition in 2019. These research results belong to Khedaioui, Douriya; Boisson, Christophe; D’Agosto, Franck; Montarnal, Damien. Quality Control of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride The article mentions the following:

While the introduction of polymers into aerogels strongly enhances their toughness, truly elastic monolithic aerogels which restore their dimensions upon extensive compression are still challenging to synthesize. In this context hydrophobic semi-crystalline polymers with low glass transition temperatures, and combined stiffness and flexibility, have only recently attracted attention. Shown here is that polyethylene aerogels with a low d., and combined chem. crosslinking and high crystallinity, display high moduli and excellent mech. resilience. To maximize the crystallinity of these aerogels while maintaining a high crosslinking d., polyethylene networks with well-defined segments were synthesized by hydrosilylation crosslinking of telechelic, vinyl-functionalized oligomers obtained from catalyzed chain-growth polymerization Recoverable deformations both above and below the melting temperature of polyethylene affords remarkable shape-memory properties. In the experiment, the researchers used 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Quality Control of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.Quality Control of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chlorideIn addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Continuous Flow Synthesis of Sulfur- and Selenium-NHC Compounds (NHC=N-Heterocyclic Carbene)》 was written by Cauwenbergh, Thibault; Scattolin, Thomas; Simoens, Andreas; Tzouras, Nikolaos V.; Stevens, Christian V.; Nolan, Steven P.. Product Details of 258278-25-0 And the article was included in European Journal of Organic Chemistry on April 21 ,2022. The article conveys some information:

The first continuous flow syntheses of sulfur- and selenium-NHC (NHC=N-heterocyclic carbene) adducts in unprecedented short reaction times and high yields are reported. The importance of these species in coordination chem. or as efficient tools for determining the π-acceptor character of NHC ligands make any improvement in their synthesis a worthy goal. Thiourea derivatives bearing both saturated and unsaturated NHCs were obtained using NEt3 as a weak base (homogeneous setup) in conjunction with a bed of elemental sulfur (S8). The synthetic route proving optimal for selenoureas involves the use of a simple Se/K2CO3 heterogeneous microreactor design. The experimental process involved the reaction of 1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0Product Details of 258278-25-0)

1,3-Bis(2,6-diisopropylphenyl)-4,5-dihydro-1H-imidazol-3-ium chloride(cas: 258278-25-0) may be used as a precursor to the free carbene 1,3-bis(2,6-diisopropylphenyl)-2-imidazolidinylidene, and also used as an in situ formed catalyst in a variety of reactions, e.g. amination, Heck coupling reaction, the ring-opening metathesis polymerization (ROMP), hydrogenation.Product Details of 258278-25-0In addition, it can efficiently catalyze the Suzuki-Miyaura coupling of aryl chlorides with aryl boronic acids.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Name: Di(1H-imidazol-1-yl)methanoneIn 2021 ,《Postmodulation of the Metal-Organic Framework Precursor toward the Vacancy-Rich CuxO Transducer for Sensitivity Boost: Synthesis, Catalysis, and H2O2 Sensing》 appeared in Analytical Chemistry (Washington, DC, United States). The author of the article were Li, Junji; Xin, Wen-Li; Dai, Yu-Xuan; Shu, Guofang; Zhang, Xue-Ji; Marks, Robert S.; Cosnier, Serge; Shan, Dan. The article conveys some information:

Metal-organic frameworks (MOFs) act as versatile coordinators for the subsequent synthesis of high-performance catalysts by providing dispersed metal-ion distribution, initial coordination condition, dopant atom ratios, and so on. In this work, a crystalline MOF trans-[Cu(NO3)2(Him)4] was synthesized as the novel precursor of a redox-alternating CuxO electrochem. catalyst. Through simple temperature modulation, the gradual transformation toward a highly active nanocomposite was characterized to ascertain the signal enhancing mechanism in H2O2 reduction Owing to the proprietary structure of the transducer material and its ensuing high activity, a proof-of-principle sensor was able to provide an amplified sensitivity of 2330μA mM-1 cm-2. The facile one-pot preparation and intrinsic nonenzymic nature also suggests its wide potentials in medical settings. In the part of experimental materials, we found many familiar compounds, such as Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Name: Di(1H-imidazol-1-yl)methanone)

Di(1H-imidazol-1-yl)methanone(cas: 530-62-1) is a coupling agent in the synthesis of dipolar polyamides for nonlinear optical applications and polypeptides. It also used to make β-keto sulfones and sulfoxides, lead sequestering agents, and β-enamino acid derivatives.Name: Di(1H-imidazol-1-yl)methanone

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Mechanochemical green synthesis of hyper-crosslinked cyclodextrin polymers》 was published in Beilstein Journal of Organic Chemistry in 2020. These research results belong to Pedrazzo, Alberto Rubin; Caldera, Fabrizio; Zanetti, Marco; Appleton, Silvia Lucia; Dahkar, Nilesh Kumar; Trotta, Francesco. Product Details of 530-62-1 The article mentions the following:

Cyclodextrin nanosponges (CD-NS) are nanostructured crosslinked polymers made up of cyclodextrins. The reactive hydroxy groups of CDs allow them to act as multifunctional monomers capable of crosslinking to bi- or multifunctional chems. The most common NS synthetic pathway consists in dissolving the chosen CD and an appropriate crosslinker in organic polar aprotic liquids (e.g., N,N-dimethylformamide or DMSO), which affect the final result, especially for potential biomedical applications. This article describes a new, green synthetic pathway through mechanochem., in particular via ball milling and using 1,1-carbonyldiimidazole as the crosslinker. The polymer obtained exhibited the same characteristics as a CD-based carbonate NS synthesized in a solvent. Moreover, after the synthesis, the polymer was easily functionalized through the reaction of the nucleophilic carboxylic group with three different organic dyes (fluorescein, methyl red, and rhodamine B) and the still reactive imidazoyl carbonyl group of the NS. In the experiment, the researchers used Di(1H-imidazol-1-yl)methanone(cas: 530-62-1Product Details of 530-62-1)

Di(1H-imidazol-1-yl)methanone(cas: 530-62-1) is a peptide coupling reagent,it is used in the synthesis of peptides. Reacts readily with carboxylic acids to form acyl imidazoles; subsequent reaction with amines to form amides goes smoothly.Product Details of 530-62-1

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

《Biotinylated photoactive Pt(II) anticancer complexes》 was published in Chemical Communications (Cambridge, United Kingdom) in 2020. These research results belong to Shi, Huayun; Imberti, Cinzia; Huang, Huaiyi; Hands-Portman, Ian; Sadler, Peter J.. COA of Formula: C10H16N2O3S The article mentions the following:

Novel biotinylated diazido-Pt(II) complexes exhibit high visible light photocytotoxicity while being stable in the dark. Photocytotoxicity and cellular accumulation of all-trans-[Pt(py)2(N3)2(biotin)(OH)] (2a) were enhanced significantly when bound to avidin; irradiation induced dramatic cellular morphol. changes in human ovarian cancer cells treated with 2a. After reading the article, we found that the author used 5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5COA of Formula: C10H16N2O3S)

5-((3aS,4S,6aR)-2-Oxohexahydro-1H-thieno[3,4-d]imidazol-4-yl)pentanoic acid(cas: 58-85-5) may be used to elute proteins from avidin/streptavidin resins. It has been used for culturing of oligodendrocytes.COA of Formula: C10H16N2O3S And it has been used for blocking endogenous biotin during immunohistology procedures.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

The author of 《Absorptimetric and fluorimetric study of solvent dependence and prototropism of 2-substituted benzimidazole derivatives》 were Sinha, Hemant K.; Dogra, Sneh K.. And the article was published in Journal of the Chemical Society, Perkin Transactions 2: Physical Organic Chemistry (1972-1999) in 1987. Quality Control of 5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole The author mentioned the following in the article:

A study of the effects of solvents on the absorption and fluorescence spectra of 2-substituted benzimidazoles showed that the lowest-energy transition of the chloromethyl, dichloromethyl, and cyanomethyl derivatives is of π-π* character, and that of the 5-chloro-2-(trichloromethyl), 2-(trifluoromethyl), and 2-chloro derivatives is of charge-transfer character. In the case of the monocations and monoanions of these compounds, the lowest-energy transitions are of charge-transfer and π-π* nature, resp. The presence of the methylene group between the benzimidazole and the heteroatom substituent reduces direct interaction; this is apparent from the study of proton-transfer reaction as well as from the spectral changes. The pKa values for these reactions in the ground and excited states were determined and discussed. MeCN quenches the fluorescence of the mono-, di-, and trichloromethyl compounds The mechanism could involve charge-transfer complexation.5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole(cas: 3584-66-5Quality Control of 5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole) was used in this study.

5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole(cas: 3584-66-5) belongs to imidazoles.Although other azole heterocycles are ubiquitous in a wide range of biologically active natural products, imidazole rings occur predominantly in the natural amino acid histidine. In addition, imidazole rings are part of unnatural cyclic peptides and are used as ester isosteres in peptidomimetic studies. Quality Control of 5-Chloro-2-(trichloromethyl)-1H-benzo[d]imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem