882187-78-2

Upstream product

• 874-39-5 7-Methyl-imidazo[1,2-a]pyridine 
• 98-80-6 phenylboronic acid 
• 695-34-1 2-Amino-4-methylpyridine 
• 122-78-1 phenylacetaldehyde 
• 536-74-3 phenylacetylene 
• 591-50-4 iodobenzene 
• 6635-33-2 7-methyltetrazolo[1,5-a]pyridine 
• 4926-28-7 2-Bromo-4-picoline 
• 5153-67-3 nitrostyrene 
• 108-90-7 chlorobenzene 
• 71-43-2 benzene 
• 932-87-6 1-Bromo-2-phenylacetylene 
• 7436-90-0 2,2-dibromostyrene 

Downstream Products

• 65964-65-0 7-methyl-2,3-dibenzimidazo[1,2-α]pyridine 

Relevant academic research and scientific papers

Cobalt-Catalyzed Direct Arylation of Imidazo[1,2-a]pyridine with Aryl Iodides

The Co(II)Cl2·6H2O catalyzed C–H activation/direct arylation of imidazo[1,2-a]pyridine with aryl/heteroaryl iodide is reported. The cost effective, ligand and additive free protocol using KOAc successfully afforded 3-arylimidazo[1,2-

Iron(II)-Based Metalloradical Activation: Switch from Traditional Click Chemistry to Denitrogenative Annulation

A unique concept for the intermolecular denitrogenative annulation of 1,2,3,4-tetrazoles and alkynes was discovered by using a catalytic amount of Fe(TPP)Cl and Zn dust. The reaction precludes the traditional, more favored click reaction between an organic azide and alkynes, and instead proceeds by an unprecedented metalloradical activation. The method is anticipated to advance access to the construction of important basic nitrogen heterocycles, which will in turn enable discoveries of new drug candidates.

Metal-free, base catalyzed oxidative amination and denitration reaction: Regioselective synthesis of 3-arylimidazo[1,2-a]pyridines

A metal-free, regioselective strategy for the synthesis of 3-arylimidazo[1,2-a]pyridines from β-nitrostyrenes and 2-aminopyridines using triethylamine as the catalyst and H2O2 (30% aq.) as the oxidant is reported. The use of an inexp

Metal- and base-free synthesis of imidazo[1,2-: A] pyridines through elemental sulfur-initiated oxidative annulation of 2-aminopyridines and aldehydes

The elemental sulfur-promoted oxidative cyclization reaction for the efficient synthesis of substituted imidazo[1,2-a]pyridines has been developed. Easily available 2-aminopyridines and aldehydes were directly assembled in a highly atom-economical fashion through oxidative annulation under metal- and base-free conditions. Besides arylacetaldehydes, aliphatic aldehydes were also compatible with this system to deliver the alkyl-substituted imidazo[1,2-a]pyridines in excellent yields with the capability of gram-scale synthesis.

Switching of Regioselectivity in a Perfluorohexyl Iodide Mediated Synthesis of Phenylimidazo[1,2-a]pyridines

3-Phenylimidazo[1,2-a]pyridines were synthesized through the perfluorohexyl iodide mediated coupling of 2-aminopyridines and phenylacetylenes. In situ iodination of the terminal alkyne by perfluorohexyl iodide reverses the polarity by generating a transient electrophilic iodoalkyne, and this alters the regioselectivity of the phenyl group. The reaction then proceeds by tandem electrophilic alkynylation and cyclization to form the fused-ring product. The protocol affords the 3-phenyl isomer with full regioselectivity and is complementary to reported methodologies for the synthesis of the 2-phenyl isomer starting from the same substrates.

N-Heterocyclic carbene-palladium(ii)-1-methylimidazole complex catalyzed direct C-H bond arylation of imidazo[1,2-a]pyridines with aryl chlorides

We herein reported the N-heterocyclic carbene-palladium(ii)-1-methylimidazole complex catalyzed direct C-H bond arylation of imidazo[1,2-a]pyridines with aryl chlorides. Under suitable conditions, all reactions between various imidazo[1,2-a]pyridines and

An arylation method for imidazo[1,2-a]pyridine

An arylation method for imidazo[1,2-a]pyridine is provided. Under nitrogen protection, the imidazo[1,2-a]pyridine shown as a formula (1), an aryl/heterocyclic aryl chloride shown as a formula (2), a catalyst that is a N-heterocyclic carbene-palladium complex, an alkaline compound and a reaction solvent are mixed and reacted at 80-150 DEG C for 12-24 h, and then a reaction solution is subjected to after-treatment to obtain a product that is arylated imidazo[1,2-a]pyridine shown as a formula (3). A novel catalyst system is developed. The catalyst is stable and easily available, and can allow the stable and cheap aryl/heterocyclic aryl chlorides to participate a reaction. The method has advantages of simple reaction operation, a low cost, a high product yield, high purity, and the like, is a novel method for synthesizing arylated imidazo[1,2-a]pyridine compounds, provides a novel route for synthesis of the compounds, and has good research value and a good industrial application prospect.

Room-temperature transition-metal-free one-pot synthesis of 3-aryl imidazo[1,2- a ]pyridines via iodo-hemiaminal intermediate

A mild and efficient one-pot synthesis of 3-aryl imidazo[1,2-a]pyridines in up to 88% yield was developed. An adduct was formed after the simple mixing of 2-amino-4-methylpyridine, 2-phenylacetaldehyde, and N-iodosuccinimide in CH2Cl2, and the structure of the adduct was characterized by 2D NMR, IR, and high-resolution mass analysis. The adduct was readily cyclized by treatment with a saturated aqueous solution of NaHCO3. The reactions proceeded to completion after several hours at room temperature.

Highly regioselective palladium-catalyzed direct cross-coupling of imidazo[1,2-a]pyridines with arylboronic acids

A highly regioselective method for the palladium-catalyzed direct cross-coupling of imidazo[1,2-a]pyridines with arylboronic acids has been developed by using O2 as oxidant. This process can be applied to a wide range of imidazo[1,2-a]pyridines and arylboronic acids with excellent C-3-regioselectivity. It provides a new way for developing CC bond-forming processes of multisubstituted imidazo[1,2-a]pyridines, which are common structural motifs in natural products and pharmaceuticals.

Pd-catalyzed oxidative cross-coupling of imidazo[1,2-a]pyridine with arenes

A facile method for direct Pd(OAc)2-catalyzed oxidative cross-coupling of unactivated imidazo[1,2-a]pyridine with simple arenes has been developed. The reaction shows good reaction efficiency, high regioselectivity, and good functional-group compatibility. This approach provides a useful protocol for the preparation of imidazo[1,2-a]pyridine-arene structure of interest in biological and pharmaceutical materials.