Category: imidazoles-derivatives

Kandimalla, Satheeshkumar Reddy published the artcileMetal-free C-N bond formations: one-pot synthesis of pyrido[2′,1′:2,3]imidazo[4,5-c]cinnolines, benzo[4′,5′]thiazolo- and thiazolo[2′,3′:2,3]imidazo[4,5-c]cinnolines, COA of Formula: C14H11BrN2, the main research area is imidazo heterocyclic cinnoline preparation regioselective; hydrazine imidazopyridinyl preparation oxidative arylation; imidazopyridine aryl diisopropyl azodicarboxylate hydrazination.

An efficient one-pot synthesis of novel pyrido[2′,1′:2,3]imidazo[4,5-c]cinnoline derivatives I (R1 = H, 10-CH3, 11-CH3, etc.; R2 = H, 3-Br, 3-OMe, etc.) has been achieved with moderate to good yields, with two C-N bond formations through C-H functionalization of 2-arylimidazo[1,2-a]pyridines II (R3 = H, 7-CH3, 8-CH3, etc.; R4 = H, 4-Br, 2,4-Cl2, etc.). The reaction proceeds via C-3 regioselective hydrazination with diisopropyl azodicarboxylate followed by oxidative N-arylation mediated by phenyliodine(III) diacetate (PIDA) in trifluoroacetic acid by means of C-H functionalization to produce pyrido[2′,1′:2,3]imidazo[4,5-c]cinnolines I. Other imidazoheterocycles such as 2-arylbenzo[d]imidazo[2,1-b]thiazoles and 6-arylimidazo[2,1-b]thiazoles, e.g., III, underwent similar transformations giving the corresponding cinnolines, e.g., IV, under transition metal-free and mild conditions.

RSC Advances published new progress about Addition reaction (hydrazination). 1023-01-4 belongs to class imidazoles-derivatives, name is 2-(4-Bromophenyl)-6-methylimidazo[1,2-a]pyridine, and the molecular formula is C14H11BrN2, COA of Formula: C14H11BrN2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Hall, Janet A. published the artcileThe induction of errors during in vitro DNA synthesis following chloroacetaldehyde-treatment of poly(dA-dT) and poly(dC-dG) templates, Application In Synthesis of 274-78-2, the main research area is chloroacetaldehyde DNA polymer reaction; polymerase DNA chloroacetaldehyde; ethenoadenine chloroacetaldehyde DNA; ethenocytosine chloroacetaldehyde DNA.

Chloroacetaldehyde [107-20-0], a rearranged metabolic product of the human carcinogen vinyl chloride, reacts with the DNA-like polymers poly(dA-dT) [26966-61-0] and poly(dC-dG) [62081-33-8] to form etheno-adducts of the adenine and cytosine bases. These treated polymers, when used as templates for Escherichia coli DNA polymerase I [9012-90-2] in an in vitro assay, show a decreased ability to direct DNA synthesis. At the same time, increased relative levels of noncomplementary nucleotides are incorporated. With the poly(dA-dT) templates, 1 dGMP residue is incorporated for every ∼60 ethenoadenine [13875-63-3] residues present, whereas no increased misincorporation of dCMP was detected. With the poly(dC-dG) templates, 1 misincorporation of dAMP or dTMP occurred in the presence of ∼30 and 80 ethenocytosine [274-78-2] residues, resp. A nearest neighbor anal. shows that with the modified poly(dC-dG) templates, the majority of the errors were incorporated opposite cytosine (or modified cytosine) bases.

Carcinogenesis published new progress about DNA Role: BIOL (Biological Study). 274-78-2 belongs to class imidazoles-derivatives, name is Imidazo[1,2-c]pyrimidine, and the molecular formula is C6H5N3, Application In Synthesis of 274-78-2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Chermahini, Alireza Najafi published the artcileTheoretical studies on the reactivity of mono-substituted imidazole ligands, Product Details of C3H3FN2, the main research area is Fukui reactivity monosubstituted imidazole ligand DFT B3LYP MP2.

The global and local quantum chem. reactivity descriptors of imidazole derivatives substituted at 2, 4, and 5 positions with different groups including electron-donating and electron-withdrawing substituents were calculated using the B3LYP/6-311++G(d,p) and MP2/6-311++G(d,p) methods. The substituents were selected to cover a wide range of electronic effects. Considering the calculated Fukui functions, both imidazole derivatives and their anions are suitable nucleophilic sites in the gas phase. For the most substituents the calculated Fukui function f-k values at the N-site are small in case of electron-releasing substituents indicating a preferred N-site for hard reaction. In contrast, large f-k values in case of electron-attracting groups indicate a preferred N-site for soft reaction. These two local descriptors predicted the reactivity of the electron-rich imidazole sequence to be 2-substituted imidazoles > 5-substituted imidazoles > 4-substituted imidazole where reactivity toward electrophilic attack at a pyridine nitrogen atom is enhanced by electron donor substituents elsewhere in the mol., due to resonance effect.

Structural Chemistry published new progress about Density functional theory, B3LYP. 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Product Details of C3H3FN2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Fabra, F. published the artcileFluoroazoles. II. Synthesis and proton and fluorine-19 NMR spectra of 2-, 4-, and 5-fluoro-1-methylimidazole, Formula: C3H3FN2, the main research area is imidazole fluoro methyl NMR; NMR fluorine fluoromethylimidazole.

The three possible ring-monofluorinated N-methylimidazoles were prepared by photochem. irradiation of the corresponding diazonium tetrafluoroborates. 5-Fluoro-1-methylimidazole was also obtained by methylation of 1-acetyl-4-fluoroimidazole. The 1H and 19F NMR spectra of these N-methylated fluoroazoles are compared, and the predominance of one tautomeric form in 4(5)-fluoroimidazole is discussed.

Journal of Heterocyclic Chemistry published new progress about NMR (nuclear magnetic resonance). 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Formula: C3H3FN2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Iaroshenko, Viktor O. published the artcileTransition-Metal-Catalyzed Arylation of Nitroimidazoles and Further Transformations of Manipulable Nitro Group, Application of 5-Bromo-2-methyl-4-nitroimidazole, the main research area is palladium nickel catalyst arylation nitroimidazole aryl bromide.

Pd- or Ni-catalyzed C-H arylation of 4-nitroimidazole derivatives directed by a manipulable nitro group was developed. The reaction tolerates a wide range of substituted aryl halides and 4-nitroimidazoles. The experiments indicated that the nitro group has influence on the regioselectivity of the reaction. In addition, we have shown that the efficiency of the Suzuki-Miyaura cross-coupling reaction of nitroimidazoles is slightly lower in comparison to the direct C-H arylation. The exploration of the chem. potential of the nitro group and a putative reaction mechanism are discussed.

Journal of Organic Chemistry published new progress about Aryl bromides Role: RCT (Reactant), RACT (Reactant or Reagent). 18874-52-7 belongs to class imidazoles-derivatives, name is 5-Bromo-2-methyl-4-nitroimidazole, and the molecular formula is C4H4BrN3O2, Application of 5-Bromo-2-methyl-4-nitroimidazole.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Kantam, M. Lakshmi published the artcileN-Arylation of heterocycles with activated chloro- and fluoroarenes using nanocrystalline copper(II) oxide, Synthetic Route of 870837-48-2, the main research area is chloroarene heterocycle nanocrystalline copper oxide N arylation; fluoroarene heterocycle nanocrystalline copper oxide N arylation; haloarene heterocycle nanocrystalline copper oxide N arylation; aryl halide imidazole nancryst copper oxide N arylation; imidazole N aryl preparation; N arylheterocycle preparation.

Nanocrystalline copper oxide was found to be an effective heterogeneous catalyst for the N-arylation of heterocycles with activated chloro- and fluoroarenes using potassium carbonate as base. N-Arylated products, e.g., I, were isolated in good to excellent yields. The catalyst can be used for five cycles with almost consistent activity.

Advanced Synthesis & Catalysis published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 870837-48-2 belongs to class imidazoles-derivatives, name is 3-Chloro-4-(1H-imidazol-1-yl)benzaldehyde, and the molecular formula is C10H7ClN2O, Synthetic Route of 870837-48-2.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

MaGee, Karen D. M. published the artcileSynthesis, Solid-state Structures, Solution Behaviour and Catalysis Studies of Nickel Complexes of Bis(benzimidazolin-2-ylidene)pyridine Pincer Ligands, SDS of cas: 72721-02-9, the main research area is crystal structure benzimidazolinylidenepyridine pincer nickel preparation catalyst Kumada coupling; mol structure benzimidazolinylidenepyridine pincer nickel preparation catalyst Kumada coupling; aryl halide Kumada Grignard catalyst benzimidazolinylidenepyridine NHC pincer nickel.

N-Heterocyclic carbene-Ni complexes with five- and four-coordinate geometries [(CNC)NiBr2] and [(CNC)NiBr]X (X = PF6 or BPh4) were prepared with the pincer ligands 2,6-bis(N-octylbenzimidazolin-2-ylidene)pyridine and 2,6-bis(N-butyl-5,6-dimethoxybenzimidazolin-2-ylidene)pyridine. The addition of the n-octyl substituent significantly extends the solubility of the complexes and has allowed UV-visible solution studies of the complexes in CH2Cl2 and MeOH. The four- and five-coordinate species exist in equilibrium in solution and this equilibrium was explored by UV-visible studies. The complexes also were characterized by NMR studies, and single crystal x-ray diffraction studies were performed on [(CNC)NiBr2] (CNC = 2,6-bis(N-octylbenzimidazolin-2-ylidene)pyridine) and [(CNC)NiBr]BPh4 (CNC = 2,6-bis(N-butyl-5,6-dimethoxybenzimidazolin-2-ylidene)pyridine). The Ni complexes displayed only moderate activity in Tamao-Kumada-Corriu coupling reactions.

Australian Journal of Chemistry published new progress about Aryl halides Role: RCT (Reactant), RACT (Reactant or Reagent). 72721-02-9 belongs to class imidazoles-derivatives, name is 5,6-Dimethoxy-1H-benzo[d]imidazole, and the molecular formula is C9H10N2O2, SDS of cas: 72721-02-9.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ohshima, Etsuo published the artcileNon-prostanoid thromboxane A2 receptor antagonists with a dibenzoxepin ring system. 2, Related Products of imidazoles-derivatives, the main research area is benzimidazolylethylidenedibenzoxepincarboxylic acid thromboxane receptor antagonist.

A series of 11-[2-(1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylic acid derivatives and related compounds were synthesized and found to be potent TXA2/PGH2 receptor antagonists. Each compound synthesized was tested for its ability to displace [3H]U-46619 binding from guinea pig platelet TXA2/PGH2 receptors. Structure-activity relationship studies revealed that the following key elements were required for enhanced activities: (1) an (E)-2-(1-benzimidazolyl)ethylidene side chain in the 11-position of the dibenzoxepin ring system and (2) a carboxyl group in the 2-position of the dibenzoxepin ring system. The studies also indicated that the TXA2/PGH2 receptor binding affinities of this series of compounds in guinea pig platelet were poorly correlated with those in human platelet. Introduction of substituent(s) to the benzimidazole moiety was effective and sodium (E)-11-[2-(5,6-dimethyl-1-benzimidazolyl)ethylidene]-6,11-dihydrodibenz[b,e]oxepin-2-carboxylate monohydrate (I) recorded the highest affinity for human platelet TXA2PGH2 receptor with a Ki value of 1.2 ± 0.14 nM. It demonstrated potent inhibitory effects on U-46619-induced guinea pig platelet aggregation (in vitro and ex vivo) and human platelet aggregation (in vitro). Compound I is a novel, orally active, and specific TXA2/PGH2 receptor antagonist with neither TXA2/PGH2 receptor agonistic nor TXA2 synthase inhibitory effects.

Journal of Medicinal Chemistry published new progress about Thromboxane receptor TBXA2R Role: SPN (Synthetic Preparation), PREP (Preparation). 72721-02-9 belongs to class imidazoles-derivatives, name is 5,6-Dimethoxy-1H-benzo[d]imidazole, and the molecular formula is C9H10N2O2, Related Products of imidazoles-derivatives.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Ray, Sibdas published the artcileStudies on the π-π stacking features of imidazole units present in a series of 5-amino-1-alkylimidazole-4-carboxamides, Computed Properties of 21343-04-4, the main research area is aminoalkylimidazolecarboxamide Pi Pi stacking distance X ray hydrogen bond.

Reaction of 2-ethoxymethyleneamino-2-cyanoacetamide with primary alkyl amines in acetonitrile solvent affords 1-substituted-5-aminoimidazole-4-carboxamides. Single crystal X-ray diffraction studies of these imidazole compounds show that there are both anti-parallel and syn-parallel π-π stackings between two imidazole units in parallel-displaced (PD) conformations and the distance between two π-π stacked imidazole units depends mainly on the anti/ syn-parallel nature and to some extent on the alkyl group attached to N-1 of imidazole; mols. with anti-parallel PD-stacking arrangements of the imidazole units have got vertical π-π stacking distance short enough to impart stabilization whereas the imidazole unit having syn-parallel stacking arrangement have got much larger π-π stacking distances. DFT studies on a pair of anti-parallel imidazole units of such an AICA lead to curves for ‘π-π stacking stabilization energy vs. π-π stacking distance’ which have got similarity with the ‘Morse potential energy diagram for a diat. mol.’ and this affords to find out a min. π-π stacking distance corresponding to the maximum stacking stabilization energy between the pair of imidazole units. On the other hand, a DFT calculation based curve for ‘π-π stacking stabilization energy vs. π-π stacking distance’ of a pair of syn-parallel imidazole units is shown to have an exponential nature.

Journal of Molecular Structure published new progress about Amides Role: PRP (Properties), SPN (Synthetic Preparation), PREP (Preparation). 21343-04-4 belongs to class imidazoles-derivatives, name is 5-Amino-1-methyl-1H-imidazole-4-carboxamide, and the molecular formula is C5H8N4O, Computed Properties of 21343-04-4.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem

Cohen, Louis Arthur published the artcilePhotochemical decomposition of diazonium fluoroborates. Application to the synthesis of ring-fluorinated imidazoles, Related Products of imidazoles-derivatives, the main research area is imidazole fluoro; diazonium fluoroborate photodecomposition; histidine fluoro.

Photochem. decomposition of imidazolediazonium fluoroborates, in fluoroboric acid solution at 10-25°, leads to ring-fluorinated imidazoles. Compounds synthesized by this method include 2-fluoroimidazole, 4-fluoroimidazole, 4 – fluoroimidazole – 5 – carboxylic acid (esters and amides), and 4-fluoro-DL-histidine. These compounds are of interest as analogs of biochem. and pharmacol. significant imidazoles.

Journal of the American Chemical Society published new progress about Diazonium compounds Role: RCT (Reactant), RACT (Reactant or Reagent). 30086-17-0 belongs to class imidazoles-derivatives, name is 5-Fluoro-1H-imidazole, and the molecular formula is C3H3FN2, Related Products of imidazoles-derivatives.

Referemce:
Imidazole – Wikipedia,
Imidazole | C3H4N2 – PubChem