Imidazo1,5apyridine synthesis organic chemistry portal. The method is a simple route for the preparation of bridgehead n heterocycles in water. The schiff bases and their metal complexes were characterized by. Therapeutically useful imidazo1,2apyridine derivatives. A highly efficient and facile method has been described for the synthesis of imidazo1,2apyridines in good to excellent yields by condensation of the. A cuicatalyzed aerobic oxidative synthesis of imidazo1,2 apyridines from 2aminopyridines and acetophenones is compatible with a broad range of functional groups. Structural commentary the molecular structure of the title complex is shown in fig. Apollo scientific home products 2 bromoimidazo1,2 apyridine. Imidazopyridine is one of the important fused bicyclic 56 heterocycles and it is recognized as a drug prejudice scaffold due to its wide range of applications in medicinal chemistry. A straightforward synthesis of 2 phenylimidazo1,2apyridine is described. Alle hochgeladenen daten werden nach 1 stunde geloscht. Activity relationship, and binding mode of an imidazo1,2.
The reaction is designed to demonstrate to students the preparation of a bridged nheterocycle, in which the heteroatom occupies a bridgehead position. Medicinal attributes of imidazo1,2apyridine derivatives. Imidazo1, 2 apyridine, sar, groebkeblackburnbienayme reaction, ugi type. Correction to discovery, structureactivity relationship. A copperiicatalyzed tandem reaction between pyridine ketone and benzylamine proceeded via an efficient condensationaminationoxidative dehydrogenation process, affording 1,3diarylated imidazo1,5apyridines in excellent yields using clean o 2 as an oxidant. Dmso and of the solvents on the synthesis of imidazo1,2 a pyridine 1d, was then studied. Medicinal attributes of imidazo1,2 apyridine derivatives. In order to prepare new imidazo1,2apyrimidines with possible pharmacological or biological properties, we have examined for the first time the action of 2amino4,5dicyanoimidazole 1 on the oxygenated heterocycles. Pdf zusammenfugen online pdf dateien zusammenfugen.
S1 supporting information a practical twostep synthesis of imidazo1,2apyridines from nprop2yn1ylpyridin2amines david sucunza,a abdelouahid samadi,a mourad chioua,a daniel b. As a result, we identified potent, selective, and orally bioavailable ask1 inhibitors for wide range of therapeutic targets. Imidazo1,2a pyridine derivatives and their application. Phosphinefree palladiumcatalyzed direct arylation of 2phenylimidazo1,2 a pyridine has been developed with the concept of using silveri carboxylate.
Synthesis of novel imidazo1,2apyridines and evaluation. Please select the one that is most appropriate for your business. Apollo scientific currently provides pricing in several currencies. With pdf merger you can merge your multiple pdf files to a single pdf file in matter of seconds. Synthesis of imidazo 1, 2 apyridine, pyrido 1, 2 apyrimidine, and 3cyanocoumarin article pdf available in monatshefte fuer chemiechemical monthly 14812 october 2017 with 86 reads. Imidazo1,2 a pyridine2carbaldehyde, imidazo1,2 a pyridine2carboxaldehyde cas number 118000434. Synthesis and characterization of 2phenylimidazo1,2a.
The product is obtained in moderate to high yield and is highly crystalline. In this process, the reaction appears to be very general and suitable for construction of a variety of imidazo1,2apyridines. The emission wavelengths of imidazo1,2apyridines increase as a function of the electronwithdrawing nature of the substituent on the c5aryl group of imidazo1,2 apyridine as a result of inductive e. In general, they are gaba a receptor agonists, however recently proton pump inhibitors. The paper deals with the recent progress realised in the comprehension of. Varying the substituent on the c3aryl group imidazo1,2 apyridine changes the homo. Cds0967 sigma aldrich imidazo1,2 a pyridine2carbaldehyde aldrich cpr. To receive a price quote on 3 iodoimidazo1,2 apyridine,please provide us with the quantity and purity percentage of the compound. By the reaction of 2benzoylmethylimidazoles 1a, b with polarized olefins 2, 3 in the presence of k2co3, the corresponding imidazo1,2 apyridine derivatives 4, 5 were obtained.
A convenient synthesis of c3aryloxymethyl imidazo1,2. Imidazo1,2 apyridine derivatives were designed, synthesized, and evaluated as inhibitors of the apoptosis signalregulating kinase 1 ask1. Synthesis and characterization of some new antimicrobial. Discovery, structureactivity relationship and binding.
Synthesis of this moiety from the easil 20th anniversary of the crsi. Green synthesis of imidazo1,2apyridines in aqueous medium. Imidazo1,2 apyridines were obtained by direct reaction of acetophenone, propiophenone, and their furan analogs and ringsubstituted derivatives with an equimolar amount of iodine and and excess 2aminopyridine or its substituted derivatives. This green chemistry approach is easy to handle, economic, nontoxic and. Imidazopyridines are important class of heterocyclic compounds. Several methods are available for the preparation of 2 or 3substituted imidazo1,2apyridines.
Cuicatalyzed synthesis of imidazo1,2apyridines from. Our heterocycles compound 2 chloroimidazo1,2 apyridine is manufactured to the highest quality standards. Use of the information, documents and data from the echa website is subject to the terms and conditions of this legal notice, and subject to other binding limitations provided for under applicable law, the information, documents and data made available on the echa website may be reproduced, distributed andor used, totally or in part, for noncommercial purposes provided that echa is. Catalystfree synthesis of imidazo 1,2a pyridines via. Synthesis of imidazo1,2apyridine derivatives and their. Due to the importance of environmentally compatible solvent in multicomponent reactions, herein we report an efficient and sustainable catalystfree synthesis of imidazo 1,2a pyridines via groebke multicomponent reaction in. Phosphinefree palladiumcatalyzed direct c3 arylation of. Design, synthesis, and biological evaluation of novel. Multicomponent synthesis of imidazo1,2apyridines using. Combine multiple pdf files into one single pdf document. Chemistry ethyl imidazo1,2 apyridine 2carboxylate hydrobromide 2 was obtained from 2aminopyridine and ethylbromopyruvate by a 2step procedure.
It was coupled with a variety of aryl alcohols in one pot to obtain a series of imidazo1,2pyridine derivatives possessing aryl ether moiety at c3 position. Compounds were prepared using a heteroaryl heck reaction procedure, involving the palladium. Our building blocks compound 3 iodoimidazo1,2 apyridine is manufactured to the highest quality standards. The effect of substituents in the ketones and 2aminopyridine, the reagent molar ratios, the character of the solvents, and replacement of iodine by. Wo2001038326a2 imidazopyridine derivatives as ligands. Covid19 is an emerging, rapidly evolving situation. Christopher housseman, xavier bock, natacha bienvenu. Our pdf merger allows you to quickly combine multiple pdf files into one single pdf document, in just a few clicks. These were based on a benzothiazole derivative that was discovered from highthroughput screening of our compound library. A class of 3phenylimidazo1,2 apyridine derivatives, substituted at the meta position of the phenyl ring by an optionally substituted aryl or heteroaryl group which is directly attached or bridged by an oxygen atom or a nh linkage, are selective ligands for gabaa receptors, in particular having high affinity for the. The coii ion is located on a twofold axis, so that half of the. Synthesis of new derivatives of 2,3dicyanoimidazo 1,2a. Multicomponent synthesis of imidazo1,2 pyridines using.
This information is stored within a cookie and setting this assumes acceptance. Another approach is the threecomponent reaction 3cr of aromatic amidines with aromatic. Imidazo1,2apyridines have already been described in the literature, for example in british pat. The present invention relates to new therapeutically useful imidazo1,2 apyridine derivatives, to a process for their preparation and to pharmaceutical compositions containing them. An imidazopyridine is a nitrogen containing heterocycle that is also a class of drugs that contain this same chemical substructure. Predicted data is generated using the us environmental protection agencys episuite. Us4382938a imidazo1,2a pyridine derivatives and their. Rapid, metalfree and aqueous synthesis of imidazo1,2a. Department of chemistry, dr b r ambedkar national institute of technology, jalandhar 144011, india. Dppi featuring different lengths of phenyl bridge, were designed and synthesized, in which imidazo 1, 2.
The compound can be purified either by direct recrystallization or silica gel column. Methylsulfinylimidazopyridine derivative 7 obtained by the reaction of 5b with mchloroperbenzoic acid mcpba, easily underwent nucleophilic substitution to. Compound 22e inhibited cmet phosphorylation and downstream signaling across. The srn1 displacements on the pyridine moiety of the imidazo1,2 apyridine being more difficult than an sn2 on the chloromethyl group, we have prepared, new reductive alkylating agents, the nitro derivatives 4a and 4b and studied their conversion with different nucleophiles to the corresponding derivatives by srn1 reactions at the sp. In this study, a selective, potent cmet inhibitor, 22e was identified, with ic 50 values of 3. Supporting information a practical twostep synthesis of. R 2 h, ch 3 with 2aminopyridines without the use of any additional catalyst and solvent. A copperiicatalyzed tandem reaction between pyridine ketone and benzylamine proceeded via an efficient condensationaminationoxidative dehydrogenation process, affording 1,3diarylated imidazo1,5 a pyridines in excellent yields using clean o 2 as an oxidant. The ring systems examined are, specifically, imidazo1,2 apyridine, imidazo1,5 apyridine and triazolo1,5 apyridine. Imidazo 1, 2 apyridine is a bicyclic system with a bridgehead nitrogen atom, of growing interest in medicinal chemistry. A series of imidazo1,2 apyridine derivatives against cmet was designed by means of bioisosteric replacement. The physical and spectroscopic data of the reported compounds were comparable with literature.
To receive a price quote on 2 chloroimidazo1,2 apyridine,please provide us with the quantity and purity percentage of the compound. Complexes have been examined by a combination of 1h and c nmr. Free web app to quickly and easily combine multiple files into one pdf online. A coppercatalyzed method for the synthesis of imidazo1,2apyridines with aminopyridines and nitroolefins using air as oxidation agent in a onepot procedure has been developed. This moiety is also useful in material science because of its structural character. The reaction also enables the formation of alkenylsubstituted imidazoheterocycles by using unsaturated ketones as substrates.