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Usage

Uses

Used in Pharmaceutical Industry:
6-Methylimidazo[1,2-a]pyridine-3-carbaldehyde is used as a key intermediate in the synthesis of various pharmaceutical compounds. Its unique molecular structure allows for the creation of a wide range of medications, making it an essential component in the development of new drugs.
Used in Organic Chemistry:
In the field of organic chemistry, 6-Methylimidazo[1,2-a]pyridine-3-carbaldehyde is utilized for various synthetic applications. Its versatility as a chemical compound enables researchers to explore new reactions and pathways, contributing to the advancement of organic chemistry.
Used in Food Industry as a Flavoring Agent:
6-Methylimidazo[1,2-a]pyridine-3-carbaldehyde is used as a flavoring agent in the food industry. It is employed in small amounts to give specific taste and aroma to certain food products, enhancing the overall sensory experience for consumers. However, due to the potential irritants associated with aldehydes, it is crucial to use 6-Methylimidazo[1,2-a]pyridine-3-carbaldehyde responsibly and within safe limits.

Upstream product

• 1603-41-4 (5-methyl-pyridin-2-yl)amine 
• 2065-75-0 2-Bromo-malonaldehyde 
• 624-67-9 Propargylic aldehyde 
• 67-68-5 dimethyl sulfoxide 
• 874-38-4 6-methylimidazo[1,2-a]pyridine 

Relevant academic research and scientific papers

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.

Heterogeneous gold(I)-catalysed annulation between 2-aminopyridines and propiolaldehydes leading to 3-acylimidazo[1,2-a]pyridines

The heterogeneous annulation between 2-aminopyridines and propiolaldehydes was achieved in CH2Cl2 at 25 °C in the presence of 3 mol% of MCM-41-immobilised phosphine gold(I) complex (MCM-41-PPh3-AuCl) and AgSbF6

Identification of the Privileged Position in the Imidazo[1,2-a]pyridine Ring of Phosphonocarboxylates for Development of Rab Geranylgeranyl Transferase (RGGT) Inhibitors

Members of the Rab GTPase family are master regulators of vesicle trafficking. When disregulated, they are associated with a number of pathological states. The inhibition of RGGT, an enzyme responsible for post-translational geranylgeranylation of Rab GTPases represents one way to control the activity of these proteins. Because the number of molecules modulating RGGT is limited, we combined molecular modeling with biological assays to ascertain how modifications of phosphonocarboxylates, the first reported RGGT inhibitors, rationally improve understanding of their structure-activity relationship. We have identified the privileged position in the core scaffold of the imidazo[1,2-a]pyridine ring, which can be modified without compromising compounds' potency. Thus modified compounds are micromolar inhibitors of Rab11A prenylation, simultaneously being inactive against Rap1A/Rap1B modification, with the ability to inhibit proliferation of the HeLa cancer cell line. These findings were rationalized by molecular docking, which recognized interaction of phosphonic and carboxylic groups as decisive in phosphonocarboxylate localization in the RGGT binding site.

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.

Design, synthesis and biological evaluation of acylhydrazone derivatives as PI3K inhibitors

Since the PI3K signaling pathway is the most commonly activated in human cancers, inhibition of PI3K is a promising approach to cancer therapy. In this study, a series of 2-methyl-5-nitrobenzeneacylhydrazones were designed and synthesized. All the new der

Transition metal-mediated C=O and C=C bond-forming reactions: A regioselective strategy for the synthesis of imidazo[1,2- A ]pyridines and imidazo[1,2- A ]pyrazines

A novel and convenient transformation for the regiospecific synthesis of functionalized imidazo[1,2-a]pyridine aldehydes/ketones and 3-vinyl imidazo[1,2-a]pyridines has been developed via copper(I)- and palladium(II)-catalyzed cyclization. The one-pot reaction proceeds smoothly with commercially available catalysts and affords the products in moderate to good yields. It represents an efficient approach for the formation of C-N, C=O, and C=C bonds under mild conditions.

Copper-catalyzed intramolecular dehydrogenative aminooxygenation: Direct access to formyl-substituted aromatic N-heterocycles

A direct synthesis of carbaldehydes through intramolecular dehydrogenative aminooxygenation has been developed. The process uses a catalytic amount of copper(II) in DMF or DMA under oxygen and does not require additional oxidants (see scheme). Mechanistic studies suggest that the carbonyl oxygen atom of the aldehyde is derived from oxygen through a copper-mediated oxygen activation process via a peroxy-copper(III) intermediate. Copyright

Synthesis and biological evaluation of sulfonylhydrazone-substituted imidazo[1,2-a]pyridines as novel PI3 kinase p110α inhibitors

We have previously reported the imidazo[1,2-a]pyridine derivative 4 as a novel p110α inhibitor; however, although 4 is a potent inhibitor of p110α enzymatic activity and tumor cell proliferation in vitro, it is unstable in solution and ineffective in vivo