65964-60-5

Usage

Uses

Used in Pharmaceutical Industry:
2-P-TOLYL-IMIDAZO[1,2-A]PYRIDINE is used as a potential drug candidate for the development of new medications due to its unique chemical structure and potential therapeutic properties.
Used in Drug Development:
2-P-TOLYL-IMIDAZO[1,2-A]PYRIDINE is used as a compound in the research and development of new drugs, particularly for the treatment of various medical conditions, as it has shown promise in preclinical studies.
Used in Materials Science:
2-P-TOLYL-IMIDAZO[1,2-A]PYRIDINE may be used as a component in the development of new materials, given its unique chemical properties and potential applications in this field.
Used in Organic Synthesis:
2-P-TOLYL-IMIDAZO[1,2-A]PYRIDINE could be utilized as a reactant or intermediate in organic synthesis processes, contributing to the creation of new organic compounds and chemical products.

InChI:InChI=1/C14H12N2/c1-11-5-7-12(8-6-11)13-10-16-9-3-2-4-14(16)15-13/h2-10H,1H3

Upstream product

• 104-87-0 4-methyl-benzaldehyde 
• 504-29-0 2-aminopyridine 
• 98475-04-8 1-(4-methylphenyl)-2-(p-tolylsulfonyloxy)ethanone 
• 622-97-9 1-ethenyl-4-methylbenzene 
• 60672-33-5 4-methyl-N'-(1-(p-tolyl)ethylidene)benzenesulfonohydrazide 
• 622-96-8 4-methylethylbenzene 
• 766-97-2 4-n-methylphenylacetylene 
• 70-11-1 α-bromoacetophenone 
• 619-41-0 4-(bromoacetyl)toluene 
• 2089-33-0 4-methylacethophenone oxime 
• 96475-75-1 4‐methylacetophenone oxime acetate 
• 4209-24-9 p-methylphenacyl chloride 
• 110-86-1 pyridine 
• 100-06-1 1-(4-methoxyphenyl)ethanone 

Downstream Products

• 3369-10-6 4-((2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methyl)morpholine 
• 1176040-39-3 (2-(p-tolyl)imidazo[1,2-a]pyridin-3-yl)methanol 
• 1417910-25-8 C₁₅H₁₃N₅ 
• 1417910-41-8 3-((4-phenyl-1H-1,2,3-triazol-1-yl)methyl)-2-p-tolyl-1H-imidazo[1,2-a]pyridine 
• 1417910-43-0 2-p-tolyl-3-((4-p-tolyl-1H-1,2,3-triazol-1-yl)methyl)-1H-imidazo[1,2-a]pyridine 
• 142016-38-4 2-(4-methylphenyl)imidazo[1,2-a]pyridine-3-carbaldehyde 
• 1310492-81-9 2-(p-tolyl)-3-(phenylthio)imidazo[1,2-a]pyridine 

Relevant academic research and scientific papers

A multi pathway coupled domino strategy: I2/ TBHP-promoted synthesis of imidazopyridines and thiazoles via sp3, sp2 and sp C-H functionalization

I2/TBHP-promoted, one-pot, multi pathway synthesis of imidazopyridines and thiazoles has been achieved through readily available ethylarenes, ethylenearenes and ethynearenes. I2/TBHP as an initiator and oxidant is used to realize the C-H functionalization of this domino reaction. Simple and available starting materials, wide range of functional group tolerance, high potential for drug activity of the products and application in production are the advantageous features of this method.

Solvent and catalyst-free synthesis of imidazo[1,2-a]pyridines by grindstone chemistry

The present work describes the solvent and catalyst-free synthesis of imidazo[1,2-a]pyridines in excellent to nearly quantitative yields from 2-aminopyridines and a wide variety of ω-bromomethylketones using a grindstone procedure at 25°C to 30°C for 3 to

Micellar Catalysis: Visible-Light Mediated Imidazo[1,2-a]pyridine C—H Amination with N-Aminopyridinium Salt Accelerated by Surfactant in Water

A light-promoted metal-free protocol for the amination of imidazo[1,2-a]pyridines with N-aminopyridinium salt by the assistance of surfactants in water was reported, charactering mild and environmentally benign conditions, as well as great functional grou

Synthetic method of imidazopyridine compounds

The invention provides a novel method for synthesizing imidazopyridine compounds. According to the invention, aminopyridine compounds and sulfur ylide are used as original reaction substrates, iron phthalocyanine (FeIIPc) is used as a catalyst, and a series of the imidazopyridine compounds are obtained under the condition that the advantages of mildness, greenness, high efficiency, wide substrateuniversality and the like are achieved.

Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines

Oxidation potential-guided electrochemical radical-radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood of successful radical-radical coupling reactions, allowing the simple and direct synthetic access to 3-sulfonylated imidazopyridines and indolizines. The developed electrochemical radical-radical cross-coupling reactions to sulfonylated N-heteroarenes boast the green synthetic nature of the reactions that are oxidant- and metal-free.

Iodine-Mediated Sulfenylation of Imidazo[1,2- a ]pyridines with Ethyl Arylsulfinates

A simple iodine-mediated approach is reported for the synthesis of sulfenylated imidazo[1,2- a ]pyridines through the reaction of imidazo[1,2- a ]pyridines with ethyl arylsulfinates under mild conditions. The reaction scope was investigated, and a plausible mechanism is proposed to elucidate the reaction process and activation mode. The results indicate that ethyl sulfinates are efficient sulfur sources for the construction of C-S bonds.

Design, synthesis and anticancer activity of sulfenylated imidazo-fused heterocycles

We report herein, the design, synthesis and study of anticancer properties of sulfenylated 2-phenylimidazo[1,2-a]pyridines and their analogues. A set of twenty sulfenylated imidazo[1, 2-a]pyridine derivatives were synthesized. Whereby elusive amendments to the imidazo[1,2-a]pyridine motif confer dramatic changes in functional affinity of a novel action to modulate anticancer activity in seven different human cancer cell lines i.e.: MDA MB 231 (breast), HepG2 (liver), Hela (cervical), A549 (lung), U87MG (glioblastoma), SKMEL-28 (skin melanoma) and DU-145 (prostate) by employing MTT assay. Among the series, compounds 4e (naphthalene), 4f (styrene) and 4h (thiomethyl) showed potent activity towards human liver cancer cells HepG2. Cell cycle analysis results revealed that these compounds arrested the cell cycle at G2/M phase and induced apoptosis in human liver cancer cells HepG2. It was further confirmed by Hoechst staining, Measurement of mitochondrial membrane potential (ΔΨm) and Annexin V-FITC assay.

Microwave-assisted synthesis and luminescent activity of imidazo[1,2-a]pyridine derivatives

In this work, a series of phenacyl bromide derivatives was synthesized and employed as key intermediate for the synthesis of substituted imidazo[1,2-a]pyridines. First, phenacyl bromide molecules were obtained from the bromination reaction of acetophenones assisted by microwave irradiation, obtaining the products 4a-v in a 15 minutes reaction with yields in the range of 50% to 99%. Subsequently, the conjugation of these molecules with 2-aminopyridine conduced to the production of imidazo[1,2-a]pyridine derivatives (7a-v) in a 60-second reaction with yields of 24% to 99%. Improved yields were determined with respect to those obtained with more tedious methodologies like thermally and mechanically assisted routes. Intense luminescence emissions in the purple and blue regions of the electromagnetic spectra were observed under UV excitation according to the nature of the substituents. This environmentally friendly methodology is expected to constitute an important class of organic compounds for the development of biomarkers, photochemical sensors, and medicinal applications.

PhI(OAc)2-mediated oxidative C[sbnd]H sulfoximination of imidazopyridines under mild conditions

A facile protocol for direct oxidative C[sbnd]N bond coupling of unactivated imidazo[1,2-a]pyridines with NH-sulfoximines was disclosed using sulfoximines as the nitrogen sources in the presence of (diacetoxy)iodobenzene (PhI(OAc)2). The reacti

Design, one-pot green synthesis and antimicrobial evaluation of novel imidazopyridine bearing pyran bis-heterocycles

Herein, we report design, one pot synthesis and antibacterial evaluation of novel imidazopyridine bearing pyran bis-heterocycles. The compounds were synthesized in an aqueous solution of gluconic acid under both conventional heating and ultrasound irradiation. The target compounds were obtained in good to moderate yields with yield of 65–88% in 20–60 min under ultrasonic irradiation. The compounds were characterized by spectroscopic methods IR, 1H NMR, 13C NMR, MS and HRMS. X-ray single crystal structure of 7i was also determined. The compounds were evaluated for antibacterial activity by measuring zone of inhibition using disk diffusion method that revealed that some compounds were inhibiting the growth of Gram +ve and Gram -ve bacteria. Result of minimum inhibitory concentration (MIC) showed that 7a, 7h & 7k from a series 7a-7k inhibited the growth of S. aureus. The minimum bactericidal concentration (MBC) value was determined for 7a, 7h & 7k. MBC/MIC ratio of the derivatives 7a, 7k & 7h suggest former two derivatives act as bactericidal agent & later act as bacteriostatic agents against Gram +ve bacteria. Haemolysis results showed that compounds are non-cytotoxic to erythrocytes.