6188-43-8

Usage

Uses

Used in Pharmaceutical Synthesis:
IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE is used as a key intermediate in the synthesis of various pharmaceuticals for its ability to form complex heterocyclic structures that are often found in biologically active molecules. Its unique structure allows for the development of new drugs with potential therapeutic applications.
Used in Agrochemical Production:
In the agrochemical industry, IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE is utilized as an intermediate in the production of compounds that can help protect crops from pests and diseases, leveraging its reactivity and structural diversity to create effective agrochemicals.
Used in Organic Chemistry Research:
As a building block for the preparation of heterocyclic compounds, IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE is used in organic chemistry research to explore novel chemical reactions and syntheses, contributing to the discovery of new organic compounds with potential applications in various fields.
Used in Drug Discovery:
Due to its potential biological activities and pharmacological properties, IMIDAZO[1,2-A]PYRIDIN-3-CARBOXALDEHYDE is employed in drug discovery processes. It serves as a starting point for designing new drug candidates that could be effective in treating various diseases and conditions, taking advantage of its unique chemical structure to modulate biological targets.

InChI:InChI=1/C8H6N2O/c11-6-7-5-9-8-3-1-2-4-10(7)8/h1-6H

Upstream product

• 274-76-0 imidazo[1,2-a]pyridine 
• 68-12-2 N,N-dimethyl-formamide 
• 74944-12-0 2,2,2-Trichloro-1-imidazo[1,2-a]pyridin-3-yl-ethanol 
• 504-29-0 2-aminopyridine 
• 63247-73-4 3-triethylgermyl-2-propyn-1-ol 
• 2717-95-5 1-(imidazo[1,2-a]pyridin-3-yl)-N,N-dimethylmethanamine 
• 2065-75-0 2-Bromo-malonaldehyde 
• 1284210-49-6 tert-butyl prop-2-yn-1-yl(pyridin-2-yl)carbamate 
• 38427-94-0 N-(tert-butoxycarbonyl)-2-aminopyridine 
• 117459-95-7 N-(prop-2-yn-1-yl)pyridin-2-amine 
• 110-18-9 N,N,N,N,-tetramethylethylenediamine 
• 67-68-5 dimethyl sulfoxide 
• 624-67-9 Propargylic aldehyde 
• 5857-45-4 3-methylimidazo[1,2-α]pyridine 

Downstream Products

• 219310-71-1 benzyl (E)-3-(imidazo<1,2-a>pyridin-3-yl)acrylate 
• 30493-06-2 2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-carbaldehyde 
• 30489-48-6 (2-(4-chlorophenyl)imidazo [1,2-a] pyridin-3-yl)methanol 
• 103845-12-1 N-((2-(4-chlorophenyl)imidazo[1,2-a]pyridine-3-yl)methyl)butyramide 
• 103844-86-6 N-((2-(4-chlorophenyl)imidazo[1,2-a]pyridin-3-yl)methyl)-N-methylbutyramide 
• 1427161-67-8 imidazo[1,2-a]pyridine-3-carbaldehyde[4-(2-hydroxy-5-methoxyphenyl)-1,3-thiazol-2-yl]-hydrazone 
• 400037-31-2 (E)-ethyl 3-(imidazo[1,2-a]pyridin-3-yl)acrylate 

Relevant academic research and scientific papers

Synthesis, chiral high performance liquid chromatographic resolution and enantiospecific activity of a potent new geranylgeranyl transferase inhibitor, 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2-phosphonopropionic Acid

3-(3-Pyridyl)-2-hydroxy-2-phosphonopropanoic acid (3-PEHPC, 1) is a phosphonocarboxylate (PC) analogue of 2-(3-pyridyl)-1- hydroxyethylidenebis(phosphonic acid) (risedronic acid, 2), an osteoporosis drug that decreases bone resorption by inhibiting farnesyl pyrophosphate synthase (FPPS) in osteoclasts, preventing protein prenylation. 1 has lower bone affinity than 2 and weakly inhibits Rab geranylgeranyl transferase (RGGT), selectively preventing prenylation of Rab GTPases. We report here the synthesis and biological studies of 2-hydroxy-3-imidazo[1,2-a]pyridin-3-yl-2- phosphonopropionic acid (3-IPEHPC, 3), the PC analogue of minodronic acid 4. Like 1, 3 selectively inhibited Rab11 vs. Rap 1A prenylation in J774 cells, and decreased cell viability, but was 33-60 × more active in these assays. After resolving 3 by chiral HPLC (>98% ee), we found that (+)-3-E1 was much more potent than (-)-3-E2 in an isolated RGGT inhibition assay, ～17 × more potent (LED 3 μM) than (-)-3-E2 in inhibiting Rab prenylation in J774 cells and >26× more active in the cell viability assay. The enantiomers of 1 exhibited a 4-fold or smaller potency difference in the RGGT and prenylation inhibition assays.

Iodine-mediated aminohalogenation-oxidation to synthesize 2-fluoroalkyl imidazole derivatives

A simple and efficient method of iodine-mediated aminohalogenation-oxidation of fluorinated N’-propargyl amidines to synthesize 2-fluoroalkyl imidazole-5-carbaldehydes was developed. This method showed good functional group compatibility and wide substrat

Copper- A nd DMF-mediated switchable oxidative C-H cyanation and formylation of imidazo[1,2-: A] pyridines using ammonium iodide

The cyanation and formylation of imidazo[1,2-a]pyridines were developed under copper-mediated oxidative conditions using ammonium iodide and DMF as a nontoxic combined cyano-group source and DMF as a formylation reagent. Mechanistic studies indicate that the cyanation of imidazo[1,2-a]pyridines proceeds through a two-step sequence: Initial iodination and then cyanation. The cyanation has a broad substrate scope and high functional group tolerance, and can be safely conducted on a gram scale. A novel copper-mediated formylation using the widely available DMF as the formylation reagent and environmentally friendly molecular oxygen as the oxidant has also been developed. This protocol also provided a convenient approach for the synthesis of clinically used saripidem. This journal is

Novel method for constructing imidazolyl[1,2-a]pyridyl-3-aldehyde by taking DMF as formylation reagent

The invention discloses a novel method for constructing imidazolyl[1,2-a]pyridyl-3-aldehyde in one step by taking DMF (N,N-dimethylformamide) as a formylation reagent. According to the method, imidazolyl[1,2-a]pyridine serves as a reactant, and the imidazolyl[1,2-a]pyridyl-3-aldehyde is constructed in one step by taking the DMF (N,N-dimethylformamide) as the formylation reagent. According to the method disclosed by the invention, the means of synthesis is novel, the reaction conditions are mild, the reaction reagent is cheap and readily available, the N,N-dimethylformamide can serve as a reaction solvent and also can serve as a formylation reagent, and thus, the method is in line with development requirements of green chemistry.

Method for synthesizing formyl-substituted imidazo[1,2a]pyridine compounds

The invention discloses a method for synthesizing formyl-substituted imidazo[1,2a]pyridine compounds. The method is carried out according to the following steps: taking a substituted pyridine allyl amine compound represented by the formula I as an initiat

Microwave-assisted synthesis of 3-formyl substituted imidazo[1,2-a]pyridines

An efficient, metal-free method for the synthesis of 3-formyl imidazo[1,2-a]pyridines is reported. The method utilises commercially available substrates and features a broad substrate scope. The intermediate enamine was isolated and a plausible reaction mechanism proposed.

Visible light induced tetramethylethylenediamine assisted formylation of imidazopyridines

A metal-free visible light induced C-3 formylation of imidazo[1,2-a]pyridine has been developed using tetramethylethylenediamine (TMEDA) as a one carbon source. An array of 3-formyl imidazo[1,2-a]pyridines with wide functionality are synthesized using rose bengal as a photosensitizer under ambient air.

Aerobic iron(III)-catalyzed direct formylation of imidazo[1,2-a]pyridine using DMSO as carbon source

A novel and efficient iron(III)-catalyzed C3-formylation reaction of imidazo[1,2-a]pyridine in an oxygen atmosphere has been developed. The method is conducted in dimethyl sulfoxide (DMSO), which serves as both the carbonyl carbon source and solvent, in the presence of acetic acid to directly generate structurally diverse 3-formylimidazo[1,2-a]pyridine derivatives in moderate to good yields.

Cu-Catalyzed selective C3-formylation of imidazo[1,2-a]pyridine C-H bonds with DMSO using molecular oxygen

Using the widely available DMSO as the formylation reagent under oxidative conditions, an efficient Cu-catalyzed C3-formylation reaction of imidazo[1,2-a]pyridine C-H bonds to directly generate structurally sophisticated 3-formyl imidazo[1,2-a]pyridine derivatives has been developed. The reaction proceeded to generate products in good yields, and used the environmentally friendly molecular oxygen as the oxidant.

Gold-catalyzed synthesis of 3-acylimidazo[1,2-a]pyridines via carbene oxidation

A convenient gold-catalyzed strategy for the synthesis of imidazo[1,2-a]pyridine derivatives has been developed via gold carbene complexes. This transformation opens a new synthetic route to a variety of 3-carbonyl-substituted imidazo[1,2-a]pyridines using air as oxidant affording the products in good yields.