38922-83-7

Upstream product

• 504-29-0 2-aminopyridine 
• 31949-21-0 bromomethyl 2-methoxyphenyl ketone 
• 579-74-8 2-Methoxyacetophenone 
• 110-86-1 pyridine 
• 75-52-5 nitromethane 
• 135-02-4 ortho-anisaldehyde 
• 767-91-9 1-ethynyl-2-methoxybenzene 
• 1021019-74-8 imidazo[1,2-a]pyridin-2-yl trifluoromethanesulfonate 
• 5720-06-9 2-Methoxyphenylboronic acid 

Downstream Products

• 1353511-93-9 2-(2-methoxyphenyl)-3-phenylimidazo[1,2-a]pyridine 
• 114570-45-5 2-methoxy-N-(pyridin-2-yl)benzamide 

Relevant academic research and scientific papers

Switching of polymorph-dependent ESIPT luminescence of an imidazo[1,2-a]pyridine derivative

(Figure Presented) Reproducible switching of the polymorph-dependent excited-state intramolecular proton-transfer (ESIPT) luminescence of an imidazo[1,2-a]pyridine between blue-green and yellow (see picture) is achieved by thermal control of its solid-sta

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.

Metal-Free Regioselective Alkylation of Imidazo[1,2- a ]pyridines with N -Hydroxyphthalimide Esters under Organic Photoredox Catalysis

A visible-light-induced direct C-H alkylation of imidazo[1,2- a ]pyridines has been developed. It proceeds at room temperature by employing inexpensive Eosin Y as a photocatalyst and alkyl N -hydroxyphthalimide (NHP) esters as alkylation reagents. A varie

Ultrasound-assisted synthesis of imidazo[1,2-a]pyridines an d sequential one-pot preparation of 3-selanyl-imidazo[1,2-a]pyridine derivatives

A simple and rapid method to synthesize imidazo[1,2-a]pyridines starting from 2-aminopyridine and 2-bromoacetophenone derivatives under ultrasonic irradiation was developed. This protocol tolerates a wide range of 2-bromoacetophenone derivatives to produce a variety of imidazo[1,2-a]pyridines in good to excellent yields. Additionally, the one-pot preparation of 3-(organylselanyl)imidazo[1,2-a]pyridines via a sequential method is presented. In this case, different diorganyl diselenides were used as starting materials to afford the corresponding coupling products in excellent yields and short reaction times under sonication. The reactions were conducted in PEG-400, a cheap and nontoxic solvent, compatible with the ultrasound conditions in an environmentally benign process.

Straightforward synthesis of various 2,3-diarylimidazo[1,2-a]pyridines in peg400 medium through one-pot condensation and C-H arylation

PEG400 is described herein as a suitable medium for the condensation of various 2-amino pyridines with α-bromo ketones. 2-Arylimidazo[1,2-a]pyridines were synthetized in a short time through microwave irradiation in moderate to excellent yields

Iron(III)-catalyzed denitration reaction: One-pot three-component synthesis of imidazo[1,2-a]pyridine derivatives

An iron(III)-catalyzed one-pot three-component cross-coupling nitration reaction of 2-aminopyridines, aldehydes and nitroalkanes, straightforwardly forms imidazo[1,2-a]pyridine derivatives and is described in this report. The system shows good functional-group tolerance and proceeds smoothly in moderate to good yields. An iron(III)-catalyzed one-pot three-component cross-coupling nitration reaction of 2-aminopyridines, aldehydes, and nitroalkane, leading to the straightforward formation of imidazo[1,2-a]pyridine derivatives has been reported. In this procedure, the starting materials are commercially available. The system shows good functional-group tolerance and proceeds smoothly in moderate to good yields. Copyright

Heterogeneously copper-catalyzed oxidative synthesis of imidazo[1,2-a]pyridines using 2-aminopyridines and ketones under ligand- and additive-free conditions

An efficient and mild heterogeneously CuCl2/nano-TiO 2-catalyzed aerobic synthesis of imidazo[1,2-a]pyridines from 2-aminopyridines and ketones has been developed using air as the oxidant in the absence of any ligands and additives. This strategy was compatible with a large range of substrates, including unactivated aryl ketones and unsaturated ketones and went through the C-H bond functionalization mechanism instead of I --assisted Ortoleva-King reaction to provide the corresponding imidazo[1,2-a]pyridines in good yields with low catalyst loading (0.8 mol%). Moreover, the heterogeneous catalyst can be successfully employed in gram-scale synthesis and reused many times without the significant loss of catalytic activity.

Tuning of excited-state intramolecular proton transfer (ESIPT) fluorescence of imidazo[1,2-a]pyridine in rigid matrices by substitution effect

2-(2′-Hydroxyphenyl)imidazo[1,2-a]pyridine (HPIP, 1) and its derivatives are synthesized, and their fluorescence properties are studied. Although all the compounds show faint dual emission (Φ ≈ 0.01), which is assigned to the normal and excited-state intr

Conversion of pyridine to imidazo[1,2-a]pyridines by copper-catalyzed aerobic dehydrogenative cyclization with oxime esters

A rapid and environmentally friendly conversion of pyridine to imidazo[1,2-a]pyridines has been developed via copper-catalyzed aerobic dehydrogenative cyclization with ketone oxime esters.

CuI-catalyzed aerobic oxidative α-aminaton cyclization of ketones to access aryl or alkenyl-substituted imidazoheterocycles

CuI-catalyzed aerobic oxidative synthesis of imidazoheterocycles has been achieved. Four hydrogen atoms were removed in one step. This protocol was compatible with a broad range of functional groups, and it has been also successfully extended to unsaturated ketones, bringing about the formation of alkenyl-substituted imidazoheterocycles, which were difficult to prepare by previous means. Preliminary mechanistic studies indicated that this reaction was most likely to proceed through a catalytic Ortoleva-King reaction. By using this method, the marketed drug Zolimidine could be prepared with 90% yield on a gram scale from commercially available materials.