2136-55-2

Upstream product

• 1824-81-3 2-Amino-6-methylpyridine 
• 536-74-3 phenylacetylene 
• 109-06-8 α-picoline 
• 35251-31-1 N-(1-phenylethylidene)-N-(4H-1,2,4-triazol-4-yl)amine 
• 98-86-2 acetophenone 
• 4636-16-2 iodoacetophenone 
• 110-05-4 di-tert-butyl peroxide 
• 4105-21-9 2-phenylimidazo[1,2-a]pyridine 
• 75-91-2 tert.-butylhydroperoxide 
• 70-11-1 α-bromoacetophenone 
• 25063-84-7 2-amino-6-methylpyridine N-oxide 
• 91538-29-3 3-chloro-6-methyl-2-phenylpyrido<1,2-a>pyrimidin-4(4H)-one 

Downstream Products

• 62135-66-4 N-(6-methylpyridin-2-yl)benzamide 
• 1201648-95-4 5-methyl-2-phenyl-5,6,7,8-tetrahydroimidazo[1,2-a]pyridine 

Relevant academic research and scientific papers

Peroxide-mediated site-specific C-H methylation of imidazo[1,2-: A] pyridines and quinoxalin-2(1 H)-ones under metal-free conditions

An effective approach to realize the direct methylation of imidazo[1,2-a]pyridines and quinoxalin-2(1H)-ones with peroxides under metal-free conditions is described. In this protocol, peroxides serve as both the radical initiator and methyl source. Methylated imidazopyridines and quinoxalin-2(1H)-ones were smoothly synthesized in moderate to good yields. A free radical reaction mechanism was proposed to describe the methylation process.

Unconventional Reactivity with DABCO-Bis(sulfur dioxide): C–H Bond Sulfenylation of Imidazopyridines

This work highlights the unexpected and unprecedented outcome of the reactivity with DABCO-bis(sulfur dioxide). The use of this reagent led to the exclusive introduction of a sulfur atom on the C-3 position of imidazopyridines instead of a sulfone group.

Iodide-Catalyzed Phosphorothiolation of Heteroarenes Using P(O)H Compounds and Elemental Sulfur

Organothiophosphates have found widespread application as biologically active compounds and synthetic intermediates in medicinal chemistry. The first transition-metal-free one-pot direct synthesis of heterocyclic phosphorothioates involving indole or imidazo[1,2-a]pyridine derivatives, elemental sulfur, and P(O)H compounds is presented. The use of NaI or KI as a catalyst, tert-butyl hydroperoxide as an oxidant, various indole and imidazo[1,2-a]pyridine derivatives are tolerant in this transformation, affording the corresponding products in good to excellent yields. Moreover, this method can be easily adapted to large-scale preparation. O,O-Diethyl S-(1-phenyl-1H-indol-3-yl) phosphorothioate presents potent anti-inflammatory activity in lipopolysaccharide (LPS)-stimulated RAW264.7 cells in a dose-dependent manner. (Figure presented.).

Enantioselective Hydrogenation of Imidazo[1,2-a]pyridines

The enantioselective synthesis of tetrahydroimidazo[1,2-a]pyridines by direct hydrogenation was achieved using a ruthenium/N-heterocyclic carbene (NHC) catalyst. The reaction forgoes the need for protecting or activating groups, proceeds with complete regioselectivity, good to excellent yields, enantiomeric ratios of up to 98:2, and tolerates a broad range of functional groups. 5,6,7,8-Tetrahydroimidazo[1,2-a]pyridines, which are found in numerous bioactive molecules, were directly obtained by this method, and its applicability was demonstrated by the (formal) synthesis of several functional molecules.

Synthesis of novel N,N-dimethyl-1-(5-methyl-2-arylimidazo[1,2-a]pyridin-3-yl) methanamine derivatives as potential antimicrobial agents

The title compounds NnN-dimethyl-l-(5-methyl-2-arylimidazo[l,2-a]pyridin-3-yl)methanamines have been synthesized by reaction of α-haloketones with 6-methylpyridin-2-amine followed by a series of multistep reactions giving the targeted compounds (4a-l). All the synthesized compounds have been screened for their in vitro antibacterial activity against E. coli, S. aureus, P. aeruginosa, S. pyogenes and antifungal activity against C. albicans, A. Niger and A. clavatus. The structures of the synthesized compounds have been confirmed by spectral data IR, 1H and 13C NMR and mass spectra. Investigation of antimicrobial activity reveals that the compounds 4b, 4c, 4d, 4e and 4j show significant activities against tested organisms as compared to standard drugs like ampicillin and griseofulvin.

Direct one-pot synthesis of zolimidine pharmaceutical drug and imidazo[1,2-a]pyridine derivatives via I2/CuO-promoted tandem strategy

An efficient one-pot synthetic protocol was developed for the synthesis of imidazo[1,2-a]pyridines from easily available starting materials: Aromatic ketones, α,β-unsaturated ketones, β-keto esters and 2-aminopyridines. The present reaction proceeded well in MeOH under the media of I2/CuO. By using this method, the marketed drug zolimidine could be prepared easily with 95% yield. All these target products were characterized by NMR, HRMS and IR spectra. Furthermore, the target compound 3fa was determined by X-ray crystallographic analysis.

Gold-catalyzed redox synthesis of imidazo[1,2-a]pyridines using pyridine N-oxide and alkynes

A mild, catalytic, atom economical synthesis of imidazo[1,2-a]pyridines has been developed: catalytic dichloro(2-pyridinecarboxylato)gold [PicAuCl 2] in the presence of an acid produces a range of imidazo[1,2-a]pyridines in good yields starting

Copper-catalyzed aerobic oxidative C-H functionalization of substituted pyridines: Synthesis of imidazopyridine derivatives

A novel, efficient, and practical method for the synthesis of imidazopyridine derivatives has been developed through the copper-catalyzed aerobic oxidative C-H functionalization of substituted pyridines with N-(alkylidene)-4H-1,2,4-triazol-4-amines. The procedure occurs by cleavage of the N-N bond in the N-(alkylidene)-4H-1,2,4-triazol-4-amines and activation of an aryl C-H bond in the substituted pyridines. This is the first example of the preparation of imidazopyridine derivatives by using pyridines as the substrates by transition-metal-catalyzed C-H functionalization. This method should provide a novel and efficient strategy for the synthesis of other nitrogen heterocycles.

Heteroaromatic imidazo[1,2-a]pyridines synthesis from C-H/N-H oxidative cross-coupling/cyclization

A novel silver-mediated highly selective C-H/N-H oxidative cross-coupling/cyclization between 2-aminopyridines and terminal alkynes has been demonstrated. This approach provided a simple way to construct heteroaromatic imidazo[1,2-a]pyridines. By using this protocol, the marketed drug zolimidine (antiulcer) could be synthesized easily.

Heteroaromatic imidazo[1,2-a]pyridines synthesis from C-H/N-H oxidative cross-coupling/cyclization

A novel silver-mediated highly selective C-H/N-H oxidative cross-coupling/cyclization between 2-aminopyridines and terminal alkynes has been demonstrated. This approach provided a simple way to construct heteroaromatic imidazo[1,2-a]pyridines. By using this protocol, the marketed drug zolimidine (antiulcer) could be synthesized easily.