4105-21-9

Usage

Purification Methods

Crystallise the indolizine from EtOH, *benzene/pet ether, hexane (m 135-136o) or cyclohexane (m 136-137o). The hydrochloride 2H2O has (m 114-116o,from H2O), and the picrate has m 228-229o (from AcOH) and 236-238o (from Me2CO). [Adams & Dix J Am Chem Soc 80 4618 1958, Beilstein 23 III/IV 1705.]

InChI:InChI=1/C13H10N2/c1-2-6-11(7-3-1)12-10-15-9-5-4-8-13(15)14-12/h1-10H

Upstream product

• 504-29-0 2-aminopyridine 
• 4316-37-4 1,1,-diethoxy-1-phenylethane 
• 532-27-4 1-chloroacetophenone 
• 70-11-1 α-bromoacetophenone 
• 6273-90-1 N-phenacyl-2-chloropyridinium bromide 
• 98-86-2 acetophenone 
• 59046-00-3 3-chloro-2-phenylpyrido<1,2-a>pyrimidin-4(4H)-one 
• 131269-69-7 1-(2-Amino-2-phenylethyl)-1,2,3,6-tetrahydropyridin 
• 110-86-1 pyridine 
• 14181-72-7 2-bromo-1-phenyl-ethanone oxime 
• 7664-41-7 ammonia 
• 68-12-2 N,N-dimethyl-formamide 
• 7257-94-5 1-phenyl-2-(p-tolylsulfonyloxy)ethanone 
• 79069-32-2 phenyl(phenylethynyl)iodonium tosylate 

Downstream Products

• 4044-95-5 2-Phenyl-3-bromoimidazo<1,2-a>pyridine 
• 3672-37-5 3-nitroso-2-phenylimidazo<1,2-a>pyridine 
• 13622-74-7 2-phenyl-3-phenylazo-imidazo[1,2-a]pyridine 
• 76458-75-8 (2-Phenyl-imidazo[1,2-a]pyridin-3-yl)-p-tolyl-diazene 
• 13542-13-7 3-(4-methoxy-phenylazo)-2-phenyl-imidazo[1,2-a]pyridine 
• 74944-13-1 2,2,2-trichloro-1-(2-phenyl-imidazo[1,2-a]pyridin-3-yl)-ethanol 
• 67292-98-2 3-nitro-2-phenylimidazo<1,2-a>pyridine 
• 64413-91-8 2-phenyl-3-chloroimidazo<1,2-a>pyridine 
• 3999-29-9 2-phenylimidazo[1,2-a]pyridin-3-amine 
• 64413-90-7 3-iodo-2-phenylimidazo[1,2-α]pyridine 
• 365213-40-7 N,N-dimethyl-1-(2-phenylimidazo[1,2-a]pyridin-3-yl)methanamine 
• 930113-31-8 2-phenyl-3-(pyridin-3-yl)imidazo[1,2-a]pyridine 
• 930113-30-7 2-phenyl-3-(m-tolyl)imidazo[1,2-a]pyridine 
• 930113-32-9 C₂₄H₁₈N₂O 

Relevant academic research and scientific papers

Synthesis and Optical Properties of Push–Push–Pull Chromophores Based on Imidazo[5,1,2-cd]indolizines and Naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines

Four series of new push–push–pull chromophores based on two types of heterocyclic cores, namely imidazo[5,1,2-cd]indolizines and naphtho[1′,2′:4,5]imidazo[1,2-a]pyridines, and two types of linear π spacers, namely diphenylacetylene and biphenyl, were prep

Synthesis of fused imidazoles based on γ-bromodypnone

A new method based on the reaction of 4-bromo-1,3-diphenyl-2-buten-1-one with heterocyclic amines was proposed for the synthesis of fused imidazoles.

Hetarenes with a bridge nitrogen atom. 6. Ambident properties of the oxazolo[3,2-a]pyridinium nucleus in reactions with nucleophiles: Prediction and experiment

We have studied the problem of ambident opening of five-membered and six-membered rings of the heteroaromatic oxazolo[3,2-a]pyridinium cation. A quantum chemical SINDO1 calculation of the energies of isomeric adducts of this cation with nucleophiles predi

One-Pot Tandem Amidation, Knoevenagel Condensation, and Palladium-Catalyzed Wacker Type Oxidation/C-O Coupling: Synthesis of Chromeno-Annulated Imidazopyridines

A direct one-pot synthesis of chromeno-annulated imidazo[1,2-a]pyridines is achieved by the reaction of 2-amino-1-(2-ethoxy-2-oxoethyl)pyridinium salts with 2-bromoarylaldehydes using Pd(TFA)2 as a catalyst and Cu(OAc)2 as an oxidant

Diversity-oriented synthesis toward aryl- And phosphoryl-functionalized imidazo[1,2-a]pyridines

We report herein an efficient synthesis of diversely polysubstituted imidazo[1,2-a]pyridines, a family of aza-heterocycles endowed with numerous biological properties, through a sequence involving two consecutive palladium-catalyzed cross-coupling reactions. First, we demonstrated that a Hirao coupling occurred straightforwardly in high yields at positions 3, 5, and 6 of imidazopyridine derivatives, giving access to a wide variety of substituted phosphonates, phosphinates, and phosphine oxides. In a second step, direct CH-arylation of phosphorylimidazopyridines with aryl halides was found to be effective and fully selective, leading to 3-aryl-substituted imidazopyridines in moderate to high yields depending on steric hindrance.

Synthesis of C3-Cyanomethylated Imidazo[1,2- a ]pyridines via Ultrasound-Promoted Three-Component Reaction under Catalyst- and Oxidant-Free Conditions

An efficient synthesis of C3-cyanomethylated imidazo[1,2-α]pyridines via ultrasound-promoted three-component reaction under catalyst-free, oxidant-free, and mild conditions has been developed. A series of C3-cyanomethylated imidazo[1,2-α]pyridines were rapidly prepared with satisfactory yields and good functional group compatibility. This strategy cloud also be applied to the synthesis of zolpidem and alpidem in short steps.

Palladium-Catalyzed C-N Coupling of Pyrazole Amides with Triazolo- And Imidazopyridine Bromides in Ethanol

An efficient palladium-catalyzed coupling between a pyrazole amide and a heteroaryl bromide was developed to enable the streamlined synthesis of a lead candidate for schizophrenia treatment. Process robustness and scalability were achieved using ethanol a

Synthetic method of imidazopyridine compounds

The invention provides a novel method for synthesizing imidazopyridine compounds. According to the invention, aminopyridine compounds and sulfur ylide are used as original reaction substrates, iron phthalocyanine (FeIIPc) is used as a catalyst, and a series of the imidazopyridine compounds are obtained under the condition that the advantages of mildness, greenness, high efficiency, wide substrateuniversality and the like are achieved.

Design, synthesis and anticancer activity of sulfenylated imidazo-fused heterocycles

We report herein, the design, synthesis and study of anticancer properties of sulfenylated 2-phenylimidazo[1,2-a]pyridines and their analogues. A set of twenty sulfenylated imidazo[1, 2-a]pyridine derivatives were synthesized. Whereby elusive amendments to the imidazo[1,2-a]pyridine motif confer dramatic changes in functional affinity of a novel action to modulate anticancer activity in seven different human cancer cell lines i.e.: MDA MB 231 (breast), HepG2 (liver), Hela (cervical), A549 (lung), U87MG (glioblastoma), SKMEL-28 (skin melanoma) and DU-145 (prostate) by employing MTT assay. Among the series, compounds 4e (naphthalene), 4f (styrene) and 4h (thiomethyl) showed potent activity towards human liver cancer cells HepG2. Cell cycle analysis results revealed that these compounds arrested the cell cycle at G2/M phase and induced apoptosis in human liver cancer cells HepG2. It was further confirmed by Hoechst staining, Measurement of mitochondrial membrane potential (ΔΨm) and Annexin V-FITC assay.

Oxidation Potential-Guided Electrochemical Radical-Radical Cross-Coupling Approaches to 3-Sulfonylated Imidazopyridines and Indolizines

Oxidation potential-guided electrochemical radical-radical cross-coupling reactions between N-heteroarenes and sodium sulfinates have been established. Thus, simple cyclic voltammetry measurement of substrates predicts the likelihood of successful radical-radical coupling reactions, allowing the simple and direct synthetic access to 3-sulfonylated imidazopyridines and indolizines. The developed electrochemical radical-radical cross-coupling reactions to sulfonylated N-heteroarenes boast the green synthetic nature of the reactions that are oxidant- and metal-free.