Category: imidazoles-derivatives

Nickel-Catalyzed Reductive Alkylation of Heteroaryl Imines was written by Turro, Raymond F.;Brandstatter, Marco;Reisman, Sarah E.. And the article was included in Angewandte Chemie, International Edition in 2022.Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde This article mentions the following:

The preparation of heterobenzylic amines, e.g., I [R¹ = H, 4-Cl, 5-F, 6-Me, etc.; R² = i-Pr, n-Bu, t-Bu, cyclopropyl, cyclobutyl, (R)-PhCHMe; R³ = H, Me, R⁴ = PhCH₂; R³ = H, R⁴ = 4-ClC₆H₄CH₂, 2,6-Me₂C₆H₃CH₂, etc.; R³R⁴ = (CH₂)₂X(CH₂)₂; X = CH₂, O, CO, NBoc], by a Ni-catalyzed reductive cross-coupling between heteroaryl imines, e.g., II, and C(sp³) electrophiles R³R⁴CHX¹ (X¹ = Cl, Br, I, phthalimidyloxycarbonyl) is reported. This umpolung-type alkylation proceeds under mild conditions, avoids the pre-generation of organometallic reagents, and exhibits good functional group tolerance. Mechanistic studies are consistent with the imine substrate acting as a redox-active ligand upon coordination to a low-valent Ni center. The resulting bis(2-imino)heterocycle·Ni complexes can engage in alkylation reactions with a variety of C(sp³) electrophiles, giving heterobenzylic amine products in good yields. In the experiment, the researchers used many compounds, for example, 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde).

1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde (cas: 3012-80-4) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Safety of 1-Methyl-1H-benzo[d]imidazole-2-carbaldehyde

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Direct polycondensation in ionic liquids was written by Lozinskaya, E. I.;Shaplov, A. S.;Vygodskii, Ya. S.. And the article was included in European Polymer Journal in 2004.Related Products of 79917-89-8 This article mentions the following:

Ionic liquids (ILs) are subject to an enormous research effort due to their unique properties, such as non-volatility, high solution and reactivity ability, etc. For the first time ILs have been used as a solvent for preparing polymers via direct polycondensation. The influence of IL’s nature and reaction parameters upon the polymer formulation has been investigated. It is shown that direct polycondensation is successfully proceeded in ILs and tri-Ph phosphite (condensing agent) without any addnl. extra components, such as LiCl and pyridine, using in similar reactions in ordinary mol. solvents. Various polyamides (η_inh=0.11-1.10 dL/g), polyamide imides (η_inh=0.48-1.41 dL/g), -hydrazides (η_inh=0.56-0.60 dL/g) and polyhydrazides (η_inh=0.71-1.32 dL/g) have been obtained in quant. yield and high mol. weight In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8Related Products of 79917-89-8).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) belongs to imidazole derivatives. Imidazole is a heterocyclic compound with a five-membered planar ring. It is amphoteric and highly polar. 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).Related Products of 79917-89-8

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Going Full Circle: Phase-Transition Thermodynamics of Ionic Liquids was written by Preiss, Ulrich;Verevkin, Sergey P.;Koslowski, Thorsten;Krossing, Ingo. And the article was included in Chemistry – A European Journal in 2011.COA of Formula: C7H13ClN2 This article mentions the following:

The authors present the full enthalpic phase transition cycle for ionic liquids (ILs) as examples of non-classical salts. The cycle was closed for the lattice, solvation, dissociation, and vaporization enthalpies of 30 different ILs, relying on as much exptl. data as was available. High-quality dissociation enthalpies were calculated at the G3 MP2 level. From the cycle, the authors could establish, for the first time, the lattice and solvation enthalpies of ILs with imidazolium ions. For vaporization, lattice, and dissociation enthalpies, the authors also developed new prediction methods in the course of their investigations. Here, as only single-ion values need to be calculated and the tedious optimization of an ion pair can be circumvented, the computational time is short. For the vaporization enthalpy, a very simple approach was found, using a surface term and the calculated enthalpic correction to the total gas-phase energy. For the lattice enthalpy, the most important constituent proved to be the calculated conductor-like screening model (COSMO) solvation enthalpy in the ideal elec. conductor. A similar model was developed for the dissociation enthalpy. According to this assessment, the typical error of the lattice enthalpy would be 9.4 kJ mol^-1, which is less than half the deviation the authors get when using the (optimized) Kapustinskii equation or the recent volume-based thermodn. (VBT) theory. In contrast, the non-optimized VBT formula gives lattice enthalpies 20 to 140 kJ mol^-1 lower than the ones assessed in the cycle, because of the insufficient description of dispersive interactions. These findings show that quantum-chem. calculations can greatly improve the VBT approaches, which were parameterized for simple, inorganic salts with ideally point-shaped charges. The authors suggest the term “augmented VBT”, or “aVBT”, to describe this kind of theor. approach. In the experiment, the researchers used many compounds, for example, 1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8COA of Formula: C7H13ClN2).

1-Methyl-3-propylimidazolium Chloride (cas: 79917-89-8) 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.COA of Formula: C7H13ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Biodiesel via in Situ Wet Microalgae Biotransformation: Zwitter-Type Ionic Liquid Supported Extraction and Transesterification was written by Bauer, Gerald;Lima, Serena;Chenevard, Jean;Sugnaux, Marc;Fischer, Fabian. And the article was included in ACS Sustainable Chemistry & Engineering in 2017.Safety of 1-Octyl-1H-imidazole This article mentions the following:

The production of biodiesel derived from microalgae is among the most forthcoming technologies that provide an ecol. alternative to fossil fuels. Herein, a method was developed that enables the direct extraction and conversion of algal oil to biodiesel without prior isolation. The reaction occurs in aqueous media catalyzed by immobilized Candida antarctica lipase B (Novozyme 435). Zwitter-type ionic liquids were used as cocatalyst to improve the selectivity and reactivity of the enzyme. In a model reaction with sunflower oil, 64% biodiesel was obtained. Applying this method to a slurry of whole-cell Chlorella zofingiensis in water resulted in 74.8% of lipid extraction, with 27.7% biotransformation products and up to 16% biodiesel. Factors that reduced the lipase activity with whole-cell algae were subsequently probed and discussed. This “in situ” method shows an improvement to existing methods, since it integrates the oil extraction and conversion into an one-pot procedure in aqueous conditions. The extraction is nondisruptive, and is a model for a greener algae to biodiesel process. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Safety of 1-Octyl-1H-imidazole).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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 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.Safety of 1-Octyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Mechanisms by Which Human DNA Primase Chooses To Polymerize a Nucleoside Triphosphate was written by Urban, Milan;Joubert, Nicolas;Purse, Byron W.;Hocek, Michal;Kuchta, Robert D.. And the article was included in Biochemistry in 2010.Formula: C8H8N2 This article mentions the following:

Human DNA primase synthesizes short RNA primers that DNA polymerase α then elongates during the initiation of all new DNA strands. Even though primase misincorporates NTPs at a relatively high frequency, this likely does not impact the final DNA product since the RNA primer is replaced with DNA. We used an extensive series of purine and pyrimidine analogs to provide further insights into the mechanism by which primase chooses whether or not to polymerize a NTP. Primase readily polymerized a size-expanded cytosine analog, 1,3-diaza-2-oxophenothiazine NTP, across from a templating G but not across from A. The enzyme did not efficiently polymerize NTPs incapable of forming two Watson-Crick hydrogen bonds with the templating base with the exception of UTP opposite purine deoxyribonucleoside. Likewise, primase did not generate base pairs between two nucleotides with altered Watson-Crick hydrogen-bonding patterns. Examining the mechanism of NTP polymerization revealed that human primase can misincorporate NTPs via both template misreading and a primer-template slippage mechanism. Together, these data demonstrate that human primase strongly depends on Watson-Crick hydrogen bonds for efficient nucleotide polymerization, much more so than the mechanistically related herpes primase, and provide insights into the potential roles of primer-template stability and base tautomerization during misincorporation. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Formula: C8H8N2).

7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6) 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. This ring system is present in important biological building blocks, such as histidine and the related hormone histamine.Formula: C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Benzimidazole- and Imidazole-Fused Selenazolium and Selenazinium Selenocyanates: Ionic Organoselenium Compounds with Efficient Peroxide Scavenging Activities was written by Banerjee, Kaustav;Bhattacherjee, Debojit;Mahato, Sulendar K.;Sufian, Abu;Bhabak, Krishna Pada. And the article was included in Inorganic Chemistry in 2021.Computed Properties of C8H8N2 This article mentions the following:

Three new classes of ionic organoselenium compounds containing cationic benzimidazolium and imidazolium ring systems with selenocyanates as counterions are described. The cyclization of N,N’-disubstituted benzimidazolium and imidazolium bromides having N-(CH₂)₂-Br and N-(CH₂)₃-Br groups in the presence of potassium selenocyanate (KSeCN) led to formation of the corresponding selenazolium selenocyanates Iâ€?sup>-SeCN [R = Me, Bn; R¹ = R² = H, R¹R² = (CH)₄; n = 1] and selenazinium selenocyanates Iâ€?sup>-SeCN [n = 2]. However, the open-chain selenocyanates with addnl. selenocyanate counterions IIâ€?sup>-SeCN were formed from the N,N’-disubstituted benzimidazolium and imidazolium bromides having N-(CH₂)₆-Br groups. Mechanistic studies were carried out to understand the feasibility of such cyclization processes in the presence of KSeCN. The compounds were studied further for their potencies to catalytically reduce H₂O₂ in the presence of thiols. Interestingly, the cyclic selenazolium Iâ€?sup>-SeCN [n = 1] and selenazinium compounds Iâ€?sup>-SeCN [n = 2] exhibited significantly higher antioxidant activities than the corresponding acyclic selenocyanates II. Selected compounds Iâ€?sup>-SeCN [R = Bn; R¹R² = (CH)₄; n = 2] and IIâ€?sup>-SeCN [R = Me; R¹R² = (CH)₄] were further evaluated for their potencies in modulating the intracellular level of reactive oxygen species (ROS) in a representative macrophage cell line (RAW 264.7). Owing to the cationic nature of compounds, they may target and scavenge mitochondrial ROS in the cellular medium. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Computed Properties of C8H8N2).

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. 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).Computed Properties of C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Tris-imidazolium and benzimidazolium ionic liquids: a new class of biodegradable surfactants was written by Al-Mohammed, Nassir N.;Duali Hussen, Rusnah Syahila;Alias, Yatimah;Abdullah, Zanariah. And the article was included in RSC Advances in 2015.Name: 1-Octyl-1H-imidazole This article mentions the following:

Based on imidazolium and benzimidazolium, two series of novel tris-cationic ionic liquid surfactants containing ester groups were synthesized simply from readily available starting materials in high yields. Biodegradability and surfactants properties of the tris-imidazolium and tris-benzimidazolium ionic liquids were investigated. Some compounds showed assembly behavior in the pure form (i.e. absence of solvent) and in the presence of polar or nonpolar solvents. These surfactants are effectively reducing the surface tension of water in the range of 28-31 mN m^-1. Through using the ‘Closed-Bottle Test’ OECD 301D, the incorporation of alkyl or Ph side chains with ester groups in the same mol. significantly improved the biodegradation compared to sodium n-dodecyl sulfate (SDS) as a reference The aliphatic alkyl side chain, i.e., Bu, hexyl, octyl, decyl and dodecyl, in both imidazolium and benzimidazolium ionic liquids had marked increasing biodegradation and phase behavior results compared to aromatic side-chains. In the experiment, the researchers used many compounds, for example, 1-Octyl-1H-imidazole (cas: 21252-69-7Name: 1-Octyl-1H-imidazole).

1-Octyl-1H-imidazole (cas: 21252-69-7) 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.Name: 1-Octyl-1H-imidazole

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Lithium chloride-imidazolium chloride melts for the coupling reactions of propylene oxide and CO₂ was written by Nguyen, Ly Vinh;Lee, Bora;Nguyen, Dinh Quan;Kang, Min-Jung;Lee, Hyunjoo;Ryu, Seol;Kim, Hoon Sik;Lee, Je Seung. And the article was included in Bulletin of the Korean Chemical Society in 2008.Formula: C7H13ClN2 This article mentions the following:

A series of lithium chloride-imidazolium chloride (LiCl-[imidazolium]Cl) melts were prepared and their catalytic activities were evaluated for the coupling reactions of propylene oxide and CO₂. At the constant mole of LiCl, the catalytic activities of LiCl-[imidazolium]Cl melts increased with increasing molar ratio of [imidazolium]Cl/LiCl up to 2, but thereafter decreased rapidly. The variation of alkyl groups on the imidazolium ring showed a negligible effect on the catalytic activity, but the number of alkyl groups present on the imidazolium cation exerts a pronounced effect. Catalysis and electrospray ionization tandem mass spectral anal. results of LiCl-[imidazolium]Cl melts imply that the activity of the melt is strongly related to the amount of LiCl₂^– generated from the melt. In the experiment, the researchers used many compounds, for example, 1-ethyl-2,3-dimethylimidazolium chloride (cas: 92507-97-6Formula: C7H13ClN2).

1-ethyl-2,3-dimethylimidazolium chloride (cas: 92507-97-6) 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. Imidazole derivatives have antibacterial, antifungal and anticancer functionality. It interacts with DNA and also binds to protein and stops cell division.Formula: C7H13ClN2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Synthesis and Toxicity Evaluation of New Pyrroles Obtained by the Reaction of Activated Alkynes with 1-Methyl-3-(cyanomethyl)benzimidazolium Bromide was written by Ivan, Beatrice-Cristina;Dumitrascu, Florea;Anghel, Adriana Iuliana;Ancuceanu, Robert Viorel;Shova, Sergiu;Dumitrescu, Denisa;Draghici, Constantin;Olaru, Octavian Tudorel;Nitulescu, George Mihai;Dinu, Mihaela;Barbuceanu, Stefania-Felicia. And the article was included in Molecules in 2021.Category: imidazoles-derivatives This article mentions the following:

A series of new pyrrole derivatives I (R = H, methoxycarbonyl, ethoxycarbonyl; R¹ = Bz, methoxycarbonyl, ethoxycarbonyl, (propan-2-yloxy)carbonyl) were designed as chem. analogs of the 1,4-dihydropyridines drugs in order to develop future new calcium channel blockers. The new tri- and tetra-substituted N-arylpyrroles I were synthesized by the one-pot reaction of 1-methyl-3-cyanomethyl benzimidazolium bromide with substituted alkynes RCCR¹ having at least one electron-withdrawing substituent, in 1,2-epoxybutane, acting both as the solvent and reagent to generate the corresponding benzimidazolium N3-ylide. The structural characterization of the new substituted pyrroles I was based on IR, NMR spectroscopy as well as on single crystal X-ray anal. The toxicity of the new compounds was assessed on the plant cell using Triticum aestivum L. species and on the animal cell using Artemia franciscana Kellogg and Daphnia magna Straus crustaceans. The compounds showed minimal phytotoxicity on Triticum rootlets and virtually no acute toxicity on Artemia nauplii, while on Daphnia magna, it induced moderate to high toxicity, similar to nifedipine. This research indicates that the newly synthesized pyrrole derivatives are promising mols. with biol. activity and low acute toxicity. In the experiment, the researchers used many compounds, for example, 1-Methylbenzimidazole (cas: 1632-83-3Category: imidazoles-derivatives).

1-Methylbenzimidazole (cas: 1632-83-3) belongs to imidazole derivatives. Imidazole is the basic core of some natural products such as histidine, purine, histamine and DNA based structures, etc. Among the different heterocyclic compounds, imidazole is better known due to its broad range of chemical and biological properties. 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. Category: imidazoles-derivatives

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

A Versatile Approach to Ullmann C-N Couplings at Room Temperature: New Families of Nucleophiles and Electrophiles for Photoinduced, Copper-Catalyzed Processes was written by Ziegler, Daniel T.;Choi, Junwon;Munoz-Molina, Jose Maria;Bissember, Alex C.;Peters, Jonas C.;Fu, Gregory C.. And the article was included in Journal of the American Chemical Society in 2013.Formula: C8H8N2 This article mentions the following:

The use of light to facilitate copper-catalyzed cross-couplings of nitrogen nucleophiles can enable C-N bond formation to occur under unusually mild conditions. In this study, we substantially expand the scope of such processes, establishing that this approach is not limited to reactions of carbazoles with iodobenzene and alkyl halides. Specifically, we demonstrate for the first time that other nitrogen nucleophiles (e.g., common pharmacophores such as indoles, benzimidazoles, and imidazoles) as well as other electrophiles (e.g., hindered/deactivated/heterocyclic aryl iodides, an aryl bromide, an activated aryl chloride, alkenyl halides, and an alkynyl bromide) serve as suitable partners. Photoinduced C-N bond formation can be achieved at room temperature using a common procedure with an inexpensive catalyst (CuI) that does not require a ligand coadditive and is tolerant of moisture and a variety of functional groups. In the experiment, the researchers used many compounds, for example, 7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6Formula: C8H8N2).

7-Methyl-1H-benzo[d]imidazole (cas: 4887-83-6) 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. Many drugs contain an imidazole ring, such as certain antifungal drugs, the nitroimidazole series of antibiotics, and the sedative midazolam.Formula: C8H8N2

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem