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Articles de revues sur le sujet « Imidazo[2 »

Auteur : Grafiati

Publié le 4 juin 2021

Mis à jour le 25 juillet 2025

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1

Balewski, Łukasz, Franciszek Sączewski, Patrick J. Bednarski, et al. "Synthesis, Structure and Cytotoxicity Testing of Novel 7-(4,5-Dihydro-1H-imidazol-2-yl)-2-aryl-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-Imine Derivatives." Molecules 25, no. 24 (2020): 5924. http://dx.doi.org/10.3390/molecules25245924.

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The appropriate 1-arylhydrazinecarbonitriles 1a–c are subjected to the reaction with 2-chloro-4,5-dihydro-1H-imidazole (2), yielding 7-(4,5-dihydro-1H-imidazol-2-yl)-2-aryl-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-imines 3a–c, which are subsequently converted into the corresponding amides 4a–e, 8a–c, sulfonamides 5a–n, 9, ureas 6a–I, and thioureas 7a–d. The structures of the newly prepared derivatives 3a–c, 4a–e, 5a–n, 6a–i, 7a–d, 8a–c, and 9 are confirmed by IR, NMR spectroscopic data, as well as single-crystal X-ray analyses of 5e and 8c. The in vitro cytotoxic potency of these comp

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2

Zhou, Qifan, Fangyu Du, Yajie Shi, Ting Fang, and Guoliang Chen. "Synthesis and Analysis of 1-Methyl-4-Phenyl-1H-Imidazol-2-Amine." Journal of Chemical Research 42, no. 12 (2018): 608–10. http://dx.doi.org/10.3184/174751918x15414286606248.

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A practical synthetic route to an important pharmaceutical intermediate 1-methyl-4-phenyl-1H-imidazol-2-amine, via a three-step sequence involving cyclisation, hydrolysis and methylation, is reported. In the process of optimisation, a novel chemical entity was isolated and confirmed to be 2,6-diphenyl-1H-imidazo[1,2-a]imidazole by MS, 1H NMR and 13C NMR. The scale-up experiment was carried out to provide 1-methyl-4-phenyl-1H-imidazol-2-amine in 27.4% total yield.

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3

Balewski, Łukasz, and Anita Kornicka. "Synthesis of the Guanidine Derivative: N-{[(7-(4,5-Dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide." Molbank 2021, no. 3 (2021): M1246. http://dx.doi.org/10.3390/m1246.

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The guanidine derivative N-{[(7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)amino](phenylamino)methylene}benzamide (3) has been obtained by the reaction of one measure of N-{[7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene]carbamothioyl}benzamide (2) with one measure of aniline in the presence of mercury(II) chloride and triethylamine in anhydrous dimethylformamide. The structure of product 3 was confirmed by 1H and 13C-NMR, infrared spectroscopy, and elemental analysis.

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4

Abdulaeva, Inna A., Kirill P. Birin, Yulia G. Gorbunova, Aslan Yu Tsivadze, and Alla Bessmertnykh-Lemeune. "Post-synthetic methods for functionalization of imidazole-fused porphyrins." Journal of Porphyrins and Phthalocyanines 22, no. 08 (2018): 619–31. http://dx.doi.org/10.1142/s1088424618500475.

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Several methods for the post-synthetic modification of imidazo[4,5-[Formula: see text]]porphyrins are reported. First, a synthetic approach to the isomeric difunctionalized porphyrins, containing two [Formula: see text]-fused 2-aryl-1[Formula: see text]-imidazole cycles at adjacent or opposite pyrrole rings of the macrocycle is developed. The core chemistry of this synthetic route is the transformation of 2-aryl-1[Formula: see text]-imidazo[4,5-[Formula: see text]]porphyrins into corresponding imidazodioxochlorins followed by Debus–Radziszewski condensation with aromatic aldehyde. Next, 2-(4-b

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5

El Abbouchi, Abdelmoula, Jamal Koubachi, Nabil El Brahmi, and Said El Kazzouli. "Direct arylation and Suzuki-Miyaura coupling of imidazo[1,2-a]pyridines catalyzed by (SIPr)Pd(allyl)Cl complex under microwave-irradiation." Mediterranean Journal of Chemistry 9, no. 5 (2019): 347–54. http://dx.doi.org/10.13171/mjc1911271124sek.

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A short and practical arylation of imidazo[1,2-a]pyridine and imidazole derivatives with aryl halides or aryl boronic acids as coupling partners was successfully carried out using phosphine-free (SIPr)Pd(allyl)Cl as the catalyst [SIPr: (N,N’-bis(2,6-diisopropylphenyl)-4,5-dihydroimidazol-2-ylidene)] ((SIPr)Pd(allyl)Cl complex). 3,6-disubstituted imidazo[1,2-a]pyridine and 5-substituted imidazole compounds were obtained in good to excellent yields in only 1h under microwave-assisted C-H arylation and Suzuki-Miyaura coupling reaction conditions.

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6

Rufaida, Farheen *. Y. Rajesh Babu 1. "SYNTHESIS AND CHEMICAL CHARACTERIZATION OF BENZIMIDAZOLE FUSED BENZOPYRAN DERIVATIVES AND EVALUATION OF THEIR ANTI-BACTERIAL POTENCY." Journal of Pharma Research 8, no. 3 (2019): 88–93. https://doi.org/10.5281/zenodo.2620330.

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<strong><em>ABSTRACT</em></strong> <strong><em>B</em></strong><em>enz-imidazole fused benzopyran derivatives were prepared by the reaction of 2-(1H-Benzo[d]Imidazol-2-yl)-1phenyl-1H-Benzo[f]chromeno-3-amine with different substituted benzaldehydes. The resulting derivatives were subjected to physical and chemical characterization. The anti-bacterial potency of the synthesized compounds was tested against a set of Gram positive and negative bacteria. The compound 9-(2-methoxyphenyl)-16-phenyl-16H-benzo[4,5]imidazo[1,2-c]benzo[5,6]chromeno[3,2-e]pyrimidine exhibited most potent activity. Detaile

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7

Cores, Ángel, Mercedes Villacampa, and J. Carlos Menéndez. "2-(3-Bromophenyl)imidazo[2,1-b]oxazole." Molbank 2023, no. 2 (2023): M1616. http://dx.doi.org/10.3390/m1616.

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The microwave-assisted reaction of 2-nitroimidazole with 3-bromophenacyl bromide in the presence of potassium carbonate as a base and dimethylformamide as a solvent afforded 2-(3-bromophenyl)imidazo[2,1-b]oxazole. The formation of this compound was explained via a domino mechanism comprising an initial N-alkylation reaction of the imidazole substrate, followed by the base-promoted deprotonation of the position adjacent to the carbonyl to give an enolate anion that finally cyclizes via an intramolecular SNAr reaction, with the loss of the nitro group as potassium nitrite. Then, the proposed 1-(

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8

Sadek, Kamal Usef, Afaf Mohamed Abdel-Hameed, Hisham A. Abdelnabi, and Yasser Meleigy. "An efficient green synthesis of novel 1H-imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives via Strecker reaction under controlled microwave heating." Green Processing and Synthesis 8, no. 1 (2019): 297–301. http://dx.doi.org/10.1515/gps-2018-0093.

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Abstract A highly efficient multi-component one-pot synthesis of novel 1H-imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives has been developed through the reaction of easily available aromatic aldehydes, benzoyl cyanide and either 2-aminoimidazole-4,5-dicarbonitrile or 3-amino-1,2,4-triazole in pyridine under controlled microwave heating. The process is environmentally friendly, is operationally simple, with short reaction time and with high yields.

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9

Barlin, GB, LP Davies, SJ Ireland, MML Ngu, and JK Zhang. "Imidazo[1,2-b]pyridazines. XII. Syntheses and Central Nervous System Activities of Some Substituted Imidazo[1,2-b]pyridazines and Related Imidazo[1,2-a]pyridines, Imidazo[1,2-a]pyrimidines and Imidazo[1,2-a]pyrazines." Australian Journal of Chemistry 45, no. 5 (1992): 877. http://dx.doi.org/10.1071/ch9920877.

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Syntheses are reported for some 6-chloro(alkoxy,alkylthio and pheny1thio)-3-benzamidomethyl-(acetamidomethyl and methoxy)-2-arylimidazo[1,2-apyridines and some corresponding imidazo- [1,2- b]pyridazines, imidazo[1,2-a[pyrimidines and imidazo[l,2-a]pyrazines. IC50 values (or percentage displacement) are reported and discussed for the displacement of [3H]diazepam from rat brain membrane by each of these compounds. The imidazo[l,2-a[pyridines were generally slightly less potent than the imidazo[l,2- b]pyridazines but considerably more potent than the corresponding imidazo[1,2-a]pyrimidines or imi

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10

Jaberi, Hamid Reza, and Hadi Noorizadeh. "Synthesis of Some Novel Fused Imidazo [2, 1-b] [1, 3] Thiazole and Imidazo [2, 1-b] Thiazolo [5, 4-d] Isoxazole Derivatives." E-Journal of Chemistry 9, no. 3 (2012): 1518–25. http://dx.doi.org/10.1155/2012/896454.

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In this work we describe the synthesis of some novel fused imidazo [2, 1-b] [1, 3] thiazole derivatives. The reaction of 1, 2-diaminoethane 1 with carbon disulphide in H2O/ETOH as solvent furnishes 4, 5-dihydro-1H-imidazol-2-thiol 2 under reflux condition. the reaction of 4,5-dihydro-1H-imidazol-2-thiol on treatment with ethylchloro acetate and aromatic aldehyde in presence of anhydrous sodium acetate and acetic acid as solvent to give (Z)-2-(arylidene)-5,6-dihydroimidazo [2,1-b] [1,3] thiazol-3(2H)-one 3a-j. Compounds 3a-j was condensed with hydroxylamine to give 3-(aryl)-2, 3, 6, 7-tetrahydr

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11

Jismy, Badr, Mohamed Akssira, Damijan Knez, Gérald Guillaumet, Stanislav Gobec, and Mohamed Abarbri. "Efficient synthesis and preliminary biological evaluations of trifluoromethylated imidazo[1,2-a]pyrimidines and benzimidazo[1,2-a]pyrimidines." New Journal of Chemistry 43, no. 25 (2019): 9961–68. http://dx.doi.org/10.1039/c9nj01982k.

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Fluoromethylated imidazo[1,2-a]pyrimidines and benzimidazo[1,2-a]pyrimidines were synthesized through Michael addition/intramolecular cyclization reaction by condensation of 2-amino imidazole derivatives with ethyl 4,4,4-trifluorobut-2-ynate and using C–O bond activation.

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12

Tan, Fen, Zheng-Zheng Meng, Xiao-Qin Xiong, Guo-Ping Zeng, and Ming-Wu Ding. "One-Pot Regioselective Synthesis of 2,5,6,7-Tetrahydroimidazo [1,2-a]imidazol-3-ones Starting from (Vinylimino)phosphoranes." Synlett 30, no. 07 (2019): 857–59. http://dx.doi.org/10.1055/s-0037-1611760.

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A new, one-pot, regioselective preparation of 2,5,6,7-tetrahydroimidazo[1,2-a]imidazol-3-ones by a sequential aza-Wittig/nucleophilic addition/cyclization reaction was developed. The aza-Wittig reactions of ethyl (2Z)-3-aryl-2-[(triphenylphosphoranylidene)amino] acrylates with aryl isocyanates produced carbodiimide intermediates that were then treated sequentially with 2-aminoethanol and tosyl chloride/triethylamine to give the corresponding (2Z)-2-[(substituted)benzylidene]-2,5,6,7-tetrahydro-3H-imidazo[1,2-a]imidazol-3-ones in good overall yields and with high regioselectivity.

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13

Veltri, Lucia, Bartolo Gabriele, Raffaella Mancuso, et al. "Palladium-Catalyzed Carbonylative Synthesis of Functionalized Benzimidazopyrimidinones." Synthesis 50, no. 02 (2017): 267–77. http://dx.doi.org/10.1055/s-0036-1591835.

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A new and convenient approach to functionalized benzimidazopyrimidinones is reported. It is based on a two-step procedure starting from readily available 1-(prop-2-yn-1-yl)-1H-benzo[d]imidazol-2-amines, consisting of a multicomponent palladium-catalyzed oxidative cyclocarbonylation–alkoxycarbonylation process, followed by base-promoted isomerization of the initially formed mixture of isomeric carbonylated products. Fair to good overall yields of the final alkyl 2-(2-oxo-1,2-dihydrobenzo[4,5]imidazo[1,2-a]pyrimidin-3-yl)acetates are obtained, using different alcohols as solvent and nucleophile

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14

Rakhmonov, R., Sh Sharipov, M. Odilzoda, B. Safarov, A. Kobilzoda, and A. Abdurakhmonov. "SYNTHESIS AND FUNCTIONALIZATION OF SOME PARA-R-PHENYLIMIDAZO[2,1-B][1,3,4]- THIADIAZOLE DERIVATIVES." East European Scientific Journal 1, no. 4(68) (2021): 54–61. http://dx.doi.org/10.31618/essa.2782-1994.2021.1.68.15.

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The article describes the synthesis of new modifications of derivatives of 6-phenyl-, 6-piodophenyl- and 6-p-bromophenylimidazo[2,1-b][1,3,4]-thiadiazoles - N -((6-(4-iodophenyl)-2-R-imidazo[2,1-b][1,3,4]-thiadiazol-5-yl)methyl)-alkyl/ heterylamine based on the Mannich reaction, bromination 2((ethylsulfonyl)methyl)-6-phenylimidazo[2,1-b][1,3,4]-thiadiazole and the structure of the resulting compounds was established on the basis of IR spectroscopy. It was shown that the presence of substituents at the 2-nd position of the thiadiazole fragment and substituents at the 5th and 6th positions of th

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15

Loubidi, M., C. Pillard, A. El Hakmaoui, P. Bernard, M. Akssira, and G. Guillaumet. "A new synthetic approach to the imidazo[1,5-a]imidazole-2-one scaffold and effective functionalization through Suzuki–Miyaura cross coupling reactions." RSC Advances 6, no. 9 (2016): 7229–38. http://dx.doi.org/10.1039/c5ra25520a.

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A pathway to new 7-bromo-1-(4-methoxybenzyl)-5-methyl-imidazo[1,5-a]imidazole-2-one was reported. The synthetic potential of this scaffold was demonstrated by displacing bromine by Suzuki–Miyaura cross-coupling reactions.

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Štefan, Leo, Ana Čikoš, Robert Vianello, Ivica Đilović, Dubravka Matković-Čalogović, and Miljenko Dumić. "Chemistry of Spontaneous Alkylation of Methimazole with 1,2-Dichloroethane." Molecules 26, no. 22 (2021): 7032. http://dx.doi.org/10.3390/molecules26227032.

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Spontaneous S-alkylation of methimazole (1) with 1,2-dichloroethane (DCE) into 1,2-bis[(1-methyl-1H-imidazole-2-yl)thio]ethane (2), that we have described recently, opened the question about its formation pathway(s). Results of the synthetic, NMR spectroscopic, crystallographic and computational studies suggest that, under given conditions, 2 is obtained by direct attack of 1 on the chloroethyl derivative 2-[(chloroethyl)thio]-1-methyl-1H-imidazole (3), rather than through the isolated stable thiiranium ion isomer, i.e., 7-methyl-2H, 3H, 7H-imidazo[2,1-b]thiazol-4-ium chloride (4a, orthorhombi

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17

Praveen, Aletti S., Hemmige S. Yathirajan, Manpreet Kaur, et al. "Different patterns of supramolecular assembly in constitutionally similar 6-arylimidazo[2,1-b][1,3,4]thiadiazoles." Acta Crystallographica Section C Structural Chemistry 70, no. 9 (2014): 920–26. http://dx.doi.org/10.1107/s2053229614018762.

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Four imidazo[2,1-b][1,3,4]thiadiazoles containing a simply-substituted 6-aryl group have been synthesized by reaction of 2-amino-1,3,4-thiadiazoles with bromoacetylarenes using microwave irradiation and brief reaction times. 6-(2-Chlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole, C10H6ClN3S, (I), 6-(2-chlorophenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole, C11H8ClN3S, (II), 6-(3,4-dichlorophenyl)imidazo[2,1-b][1,3,4]thiadiazole, C10H5Cl2N3S, (III), and 6-(4-fluoro-3-methoxyphenyl)-2-methylimidazo[2,1-b][1,3,4]thiadiazole, C12H10FN3OS, (IV), crystallize withZ′ values of 2, 1, 1 and 2 respectively.

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18

Zlatoidský, Pavol, Elisa Martinelli, Emil Svensson, and Alexis Pruvost. "A Facile Access to Novel (5+5) Annellated Heterocycles: Synthesis of a Furopyrrole, an Imidazoimidazole and a Pyrroloimidazole." Synthesis 51, no. 18 (2019): 3491–98. http://dx.doi.org/10.1055/s-0039-1689916.

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We describe the synthesis of an ethyl 3-aryl-6H-furo[2,3-b]pyrrole-5-carboxylate 2, a 5-aryl-1H-imidazo[1,2-a]imidazole 3, and an ethyl-1-aryl-1,4-dihydropyrrolo[2,3-d]imidazole-5-carboxylate 4 as new hinge-binding motifs for PI3K kinase inhibitors. A key reaction for the formation of 2 and 4 is the Hemmetsberger–Knittel cyclization of acryloazides. The core of 3 is accessible through reaction of an α-haloketone with 2-aminoimidazole.

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19

Shukla, Upendra K., Raieshwar Singh, J. M. Khanna, et al. "Synthesis of trans-2-[N-(2-Hydroxy-1,2,3,4-tetrahydronaphthalene-1-yl)]iminothiazolidine and Related Compounds - A New Class of Antidepressants." Collection of Czechoslovak Chemical Communications 57, no. 2 (1992): 415–24. http://dx.doi.org/10.1135/cccc19920415.

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Antiparasitic and antidepressant activities exhibited by tetramisole (I) and its enantiomers prompted the study of its structural analogs trans-2-[N-(2-hydroxy-1,2,3,4-tetrahydronaphthalene/indane-1-yl)]iminothiazolidine (VIII/IX) and 2,3,4a,5,6,10b-hexahydronaphtho[1',2':4,5]-imidazo[2,1-b]thiazole (XII), 2,3,4a,5-tetrahydro-9bH-indeno[1',2':4,5]imidazo[2,1-b]thiazole (XIII), and 2,3,4a,5-tetrahydro-9bH-indeno[1',2':4,5]imidazo[2,1-b]thiazole (XVI), and a homolog 3,4,6,7-tetrahydro-7-phenyl-2H-imidazo[2,1-b]-1,3-thiazine (XX). While none of these compounds showed any noteworthy antiparasitic

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20

Kona, Sridevi, Rama Suresh Ravi, Manab Chakravarty, and Venkata N. R. Chava. "Phosphine-Free Palladium-Catalyzed Direct C-3 Arylation of 2-Phenylimidazo[1,2-a]pyridine Using Silver(I) Carboxylate." Journal of Chemistry 2013 (2013): 1–7. http://dx.doi.org/10.1155/2013/305934.

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Phosphine-free palladium-catalyzed direct arylation of 2-phenyl-imidazo[1,2-a]pyridine has been developed with the concept of using silver(I) carboxylate. This protocol efficiently catalyzes the C-H arylation of 2-phenyl-imidazo[1,2-a]pyridine with aryl iodides to afford the corresponding 2-phenyl-3-aryl-imidazo[1,2-a]pyridines in moderate to-good yields.

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Sharma, Nidhi, Sanjeev Kumar, Sangit Kumar, S. K. Mehta, and K. K. Bhasin. "Synthesis and characterization of fused imidazole heterocyclic selenoesters and their application for chemical detoxification of HgCl2." New Journal of Chemistry 42, no. 4 (2018): 2702–10. http://dx.doi.org/10.1039/c7nj03908e.

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Kolar, Patrik, and Miha Tišler. "A New Route to Imidazo(1,5-a)pyridines and -quinolines." Zeitschrift für Naturforschung B 46, no. 8 (1991): 1110–12. http://dx.doi.org/10.1515/znb-1991-0822.

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JAG, MOHAN, S. R. ANJANBYULU G., and KIRAN. "Heterocyclic Systems containing Bridgehead Nitrogen Atom. Synthesis of Thiadiazolo[2',3', : 2,1 )imidazo[ 4,5-b)quinoxaline, Jmidazo[2,1-b ]-1,3,4-thiadiazoles and their Brominated Products." Journal of Indian Chemical Society Vol. 66, Feb 1989 (1989): 118–19. https://doi.org/10.5281/zenodo.6303535.

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Department of Chemistry, Maharshi Dayanand University, Rohtak-124 001 <em>Manuscript received 25 March 1988, accepted 2 November 1988</em> 2-Amino-5-alkylthiadiazoles (1) condense with \(\propto\)-haloketones and 2,3-dichloroquinoxalene to furnish respectively the cyclised products, 2,6-disubstituted imidazo [2,1-b]-1,3,4-thiadiazoles (2) and 2-substituted-thiadiazolo(2<em>',</em>3<em>'</em>: 2,1] imidazo[4,5-b]- quinoxaline (4). Bromination of 2 furnishes 5-bromo-2,6-disubstituted-imidazo[2,1-b]- thiadiazoles (3). The antimicrobial activities of some of the compounds have be

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24

Chang, Qing, Zhongjie Wu, Lu Yu, Ping Liu, and Peipei Sun. "Visible-light-mediated C3-azolylation of imidazo[1,2-a]pyridines with 2-bromoazoles." Organic & Biomolecular Chemistry 15, no. 25 (2017): 5318–24. http://dx.doi.org/10.1039/c7ob00883j.

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Barlin, Gordon B., Les P. Davies, and Peter W. Harrison. "Imidazo[1,2-b]pyridazines. XXI. Syntheses of some 3-Acylaminomethyl-6-(chloro and iodo)- 2-(substituted phenyl)-imidazo[1,2-b]pyridazines and -imidazo[1,2-a]pyridines and their Interaction with Central and Mitochondrial Benzodiazepine." Australian Journal of Chemistry 50, no. 1 (1997): 61. http://dx.doi.org/10.1071/c96130.

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A series of 3-acylaminomethyl-6-(chloro, iodo and methyl)-2-(phenyl, 4′-t-butylphenyl, 4′-cyclohexyl- phenyl, biphenyl-4′-yl, 4′-chlorophenyl and 4′-iodophenyl)imidazo[1,2-b]pyridazines and imidazo[1,2- a]pyridines has been prepared and examined for interaction with central and mitochondrial (peripheral- type) benzodiazepine receptors. The imidazo[1,2-b]pyridazines were generally more selective for the mitochondrial receptors than the corresponding imidazo[1,2-a]pyridines. Of these compounds, 3- acetamidomethyl-2-(biphenyl-4′-yl)-6-chloroimidazo[1,2-b]pyridazine (9) proved to be the most selec

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Zhu, Jingyun, Ziyue Chen, Meng He, et al. "Metal-free electrochemical C3-sulfonylation of imidazo[1,2-a]pyridines." Organic Chemistry Frontiers 8, no. 14 (2021): 3815–19. http://dx.doi.org/10.1039/d1qo00348h.

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An electrochemical C3-sulfonylation of imidazo[1, 2-a]pyridines with sodium benzenesulfinate has been developed, providing an straightforward protocol towards biologically and synthetically useful 3-(arylsulfonyl)imidazo[1, 2-a]pyridine.

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M., J. Ladani, D. Tala S., D. Akbari J., F. Dhaduk M. та S. Joshi H. "Synthesis and biological study of oxopyrimidines and thiopyrimidines of 2-(2,4-dichlorophenyl)imidazo[1,2-α ]pyridin-3-carbaldehyde". Journal of Indian Chemical Society Vol. 86, Jan 2009 (2009): 104–8. https://doi.org/10.5281/zenodo.5807328.

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Department of Chemistry, Saurashtra University, Rajkot-360 005, Gujarat, India <em>E-mail</em> : drhsjoshi49@gmail.com <em>Manuscript received 14 November 2007, revised 6 August 2008, accepted 17 September 2008</em> 2-(2,4-Dichlorophenyl)imidazo[1,2-α]pyridlne-3·carbaldehyde (1) was prepared from 2-aminopyridine through multi-step reaction. Compound 1 reacts with different aryl ketones in the presence of catalytic amount of 40% KOH to give (2<em>E</em>)-3-[2-(2,4-dichlorophenyl)imidazo[1,2-α]pyridin-3-yl]-1-arylprop-2-en-1-ones (2a-j), which on cyclization with urea and

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Schmitt, Martine, Jean-Jacques Bourguignon, Gordon B. Barlin, and Les P. Davies. "Imidazo[1,2-b]pyridazines. XXIII Some 5-Deaza Analogues. Syntheses of Some 2-Aryl-6-(chloro, methoxy or unsubstituted)-3- (variously substituted)imidazo[1,2-a]pyridines and Their Affinity for Central and Mitochondrial Benzodiazepine Receptor." Australian Journal of Chemistry 50, no. 7 (1997): 719. http://dx.doi.org/10.1071/c97004.

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The syntheses of ethyl {2′-aryl-6′-(chloro, methoxy and unsubstituted)imidazo[1,2-a]pyridin-3′-yl}-2- (acylamino, acetoxy and hydroxy)acetates, 3-benzamidomethyl-2-benzoyl-6-(chloro and methoxy)imidazo-[1,2-a]pyridines, 3-amino-6-chloro-2-phenylimidazo[1,2-a]pyridine and ethyl 2-(2′-phenylimidazo[1,2-a]pyridin-3′-yl)acetate are reported. The ability of these compounds to displace [3H]diazepam from central and mitochondrial (peripheral-type) benzodiazepine receptors has been examined. Ethyl 2-benzamido-2-{6′-chloro-2′-(4′′-chlorophenyl)imidazo[1,2-a]pyridin-3′-yl} acetate (21) was selective for

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29

Yu, Yongping, Hassan M. El Abdellaoui, John M. Ostresh, and Richard A. Houghten. "Solid phase synthesis of [3,5,7]-1H-imidazo[1,5-a]imidazol-2(3H)-ones." Tetrahedron Letters 42, no. 4 (2001): 623–25. http://dx.doi.org/10.1016/s0040-4039(00)02022-0.

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30

Schmitt, Martine, Jean-Jacques Bourguignon, Gordon B. Barlin, and Les P. Davies. "Imidazo[1,2-b]pyridazines. XXIV Syntheses of Some 3-(Variously Substituted) Imidazo[1,2-b] pyridazines, 6-Substituted 2-Benzoyl- imidazo[1,2-b]pyridazines and Pyrimido[1,2-b]pyridazin- 5-ium-3-olates and their Interaction with Central and Mitochondrial Benzodiazepine Receptors." Australian Journal of Chemistry 50, no. 8 (1997): 779. http://dx.doi.org/10.1071/c97030.

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The syntheses of some ethyl 2-{2′-aryl-6′-(chloro, iodo and methoxy)imidazo[1,2-b]pyridazin-3′-yl}-2-(acetoxy, acylamino, hydroxy and methoxy)acetates, 6-methyl-2-(p-tolyl)- and 6-chloro-2-(4′-chlorophenyl)-3-trimethylammoniomethylimidazo[1,2-b]pyridazine iodides (and reactions thereof), 2-benzoyl 6-substituted imidazo[1,2-b]pyridazines and 7-(methoxy, chloro and phenylthio)-2-phenylpyrimido-[1,2-b]pyridazin-5-ium-3-olates are reported. The ability of these compounds to displace [3H]diazepam from rat forebrain membrane [central benzodiazepine receptor (BZR)] and rat kidney membrane [mitochondr

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31

Aginagalde, Maialen, Yosu Vara, Ana Arrieta, et al. "Tandem [8 + 2] Cycloaddition−[2 + 6 + 2] Dehydrogenation Reactions Involving Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines." Journal of Organic Chemistry 75, no. 9 (2010): 2776–84. http://dx.doi.org/10.1021/jo9022815.

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32

Il’inykh, E., and V. Sharutin. "Synthesis and study of the structure of iodine-containing imidazo[2,1-b][1,3]thiazinium systems." Bulletin of the South Ural State University series "Chemistry" 16, no. 1 (2024): 108–17. http://dx.doi.org/10.14529/chem240108.

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Heterocyclization of S-alkenyl derivatives of 1-methylimidazole-2-thiol (1-methyl-2-prenyl-sulfanylimidazole (1), 1-methyl-2-cinnamylsulfanylimidazole (4), and 2-(3-butenyl)sulfanyl-1-methyl-imidazole (7)) has been studied for the first time under the action of iodine (iodocyclization) in various solvents (chloroform, dichloro-methane, glacial acetic acid), and at different substrate and iodine ratios (1 : 1, 1 : 2). It has been found that the interaction of compounds 1, 4, 7 with iodine proceeds regioselectively, regardless of the reaction conditions, and it is accompanied by the linear annel

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33

JAG, MOHAN, S. R. ANJANBYULU G., and KIRAN. "Heterocyclic Systems containing Bridgehead Nitrogen Atom. Synthesis of Thiadiazolo[2′,3′: 2,1]imidazo[4,5-b]quinoxaline, Iiniclazo[2, 1 -1)]-1,3,4-thiadiazoles and their Brominated Products." Journal of Indian Chemical Society Vol. 66, Feb 1989 (1989): 118–19. https://doi.org/10.5281/zenodo.5959418.

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Department of Chemistry, Maharshi Dayanaud University, Rohtak-121 001 <em>Manuscript received 28 March 1988, accepted 2 November 1988</em> <strong>2-Amino-5-alkylthiadiazoles (1) condense with\(\propto\)-haloketones and 2,3-dichioro</strong><strong>quinoxalene to furnish respectively the cyclised </strong><strong>products, 2,6-disubstituted imidazo [2,1-b]-1,3,4-thiadiezoles (2) </strong><strong>and 2-substituted-thiadiazolo2</strong><strong>ʹ</strong><strong>,3</strong><strong><sup>′</sup></strong><strong> : 2,1]imidazo[4,5-b</strong><strong>ʹ</strong><strong>- quinoxaline (4). Bro

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34

Ge, Qingmei, Bin Li, Haibin Song, and Baiquan Wang. "Rhodium(iii)-catalyzed cascade oxidative annulation reactions of aryl imidazolium salts with alkynes involving multiple C–H bond activation." Organic & Biomolecular Chemistry 13, no. 28 (2015): 7695–710. http://dx.doi.org/10.1039/c5ob00823a.

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The cascade oxidative annulation reactions of aryl imidazolium salts with alkynes proceed efficiently in the presence of [Cp*RhCl<sub>2</sub>]<sub>2</sub> and Cu(OAc)<sub>2</sub>·H<sub>2</sub>O to give substituted imidazo[1,2-a]-quinolinium salts and benzo[ij]imidazo[2,1,5-de]quinolizinium salts.

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35

Kandimalla, Satheeshkumar Reddy, and Gowravaram Sabitha. "Correction: Metal-free C–N bond formations: one-pot synthesis of pyrido[2′,1′:2,3]imidazo[4,5-c]cinnolines, benzo[4′,5′]thiazolo- and thiazolo[2′,3′:2,3]imidazo[4,5-c]cinnolines." RSC Advances 6, no. 75 (2016): 70732. http://dx.doi.org/10.1039/c6ra90062c.

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Correction for ‘Metal-free C–N bond formations: one-pot synthesis of pyrido[2′,1′:2,3]imidazo[4,5-c]cinnolines, benzo[4′,5′]thiazolo- and thiazolo[2′,3′:2,3]imidazo[4,5-c]cinnolines’ by Satheeshkumar Reddy Kandimalla et al., RSC Adv., 2016, 6, 67086–67095.

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36

Shi, Benyi, Zhouhe Zhu, Yi-Shuo Zhu, et al. "Approach for 2-(arylthio)imidazoles and imidazo[2,1-b]thiazoles from imidazo[2,1-b][1,3,4]thiadiazoles by ring-opening and -reconstruction." Organic & Biomolecular Chemistry 14, no. 10 (2016): 2978–84. http://dx.doi.org/10.1039/c6ob00102e.

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37

Sharma, Gyanendra Kumar, Gurvinder Pal Singh, Harsh Bhardwaj, et al. "Microwave-assisted synthesis of some new 2-(substituted phenyl)-3-(thiazol-2-yl)imidazo[4,5-b]indoles of biological interest." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 34, no. 03 (2024): 373. http://dx.doi.org/10.59467/ijhc.2024.34.373.

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In the present investigation, we have synthesized some new 2-(substituted phenyl)-3-(thiazol-2-yl) imidazo[4,5-b]indoles (1b-8b) of biological interest. In the last step of the synthesis, N-(substituted benzylidene)thiazole-2- amines (1a-8a) were reacted with isatin and ammonium acetate using silica gel as the solid support to yield the corresponding substituted thiazolyl imidazo indole derivatives (1b-8b). The reactions were carried out by two different techniques - conventional and microwave irradiation. The microwave irradiation method offers excellent yield, lesser reaction time, and eco-e

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38

Delaye, Pierre-Olivier, Mélanie Pénichon, Leslie Boudesocque-Delaye, Cécile Enguehard-Gueiffier, and Alain Gueiffier. "Natural Deep Eutectic Solvents as Sustainable Solvents for Suzuki–Miyaura Cross-Coupling Reactions Applied to Imidazo-Fused Heterocycles." SynOpen 02, no. 04 (2018): 0306–11. http://dx.doi.org/10.1055/s-0037-1610400.

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Herein, we present the first Suzuki–Miyaura cross-coupling in a sustainable natural deep eutectic solvent (NaDES) applied to biologically relevant imidazo-fused scaffolds imidazo[1,2-a]pyridine and imidazo[1,2-b]pyridazine. The choline chloride/glycerol (1:2, mol/mol) NaDES allowed the functionalisation of diverse positions on the heterocycles with various boronic acids, by using 2.5 mol% of readily available Pd(OAc)2. Notably, the catalytic system proceeds without any ligands or additives, without protection from the atmosphere.

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JAG, MOHAN, S. R. ANJANBYULU G. та KIRAN. "Heterocyclic Systems containing Bridgehead Nitrogen Atom. Synthesis of Thiadiazolo[2ʹ3′: 2,1]imidazo[4,5-b]quinoxaline, Iiniclazo[2, 1 -b)]-1,3,4-thiadiazoles and their Brominated Products". Journal of Indian Chemical Society Vol. 66, Feb 1989 (1989): 118–19. https://doi.org/10.5281/zenodo.5995035.

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Department of Chemistry, Maharshi Dayanaud University, Rohtak-121 001 <em>Manuscript received 28 March 1988, accepted 2 November 1988</em> <strong>2-Amino-5-alkylthiadiazoles (1) condense with \(\propto\)-haloketones and 2,3-dichioro</strong><strong>quinoxalene to furnish respectively the cyclised </strong><strong>products, 2,6-disubstituted imidazo [2,1-b]-1,3,4-thiadiezoles (2) </strong><strong>and 2-substituted-thiadiazolo[2</strong><strong>ʹ</strong><strong>,3</strong><strong><sup>′</sup></strong><strong> : 2,1]imidazo[4,5-b<sup>1</sup>- quinoxaline (4). Bromination of 2 </stron

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40

Semwal, Rashmi, Gaurav Badhani, and Subbarayappa Adimurthy. "Pd-catalyzed annulation of imidazo[1,2-a]pyridines with coumarins and indoles: synthesis of benzofuran and indole fused heterocycles." Chemical Communications 58, no. 10 (2022): 1585–88. http://dx.doi.org/10.1039/d1cc06803b.

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Palladium-catalyzed annulation of 2-arylimidazo[1,2-a]pyridines for the synthesis of benzofuro[3,2-a]imidazo[5,1,2-cd]indolizines and 6-methyl-6H-imidazo[5′,1′,2′:3,4,5]indolizino[1,2-b]indoles with coumarins and N-methyl indoles has been described.

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41

O’Neill, Luke, Laura Perdisatt, and Christine O’Connor. "Structure-Property Relationships for a Series of Ruthenium(II) Polypyridyl Complexes Elucidated through Raman Spectroscopy." Journal of Spectroscopy 2018 (November 1, 2018): 1–11. http://dx.doi.org/10.1155/2018/3827130.

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A series of ruthenium polypyridyl complexes were studied using Raman spectroscopy supported by UV/Vis absorption, luminescence spectroscopy, and luminescence lifetime determination by time-correlated single photon counting (TCSPC). The complexes were characterised to determine the influence of the variation of the conjugation across the main polypyridyl ligand. The systematic and sequential variation of the main polypyridyl ligand, 2-(4-formylphenyl)imidazo[4,5-f][1,10]phenanthroline (FPIP), 2-(4-cyanophenyl)imidazo[4,5-f][1,10]phenanthroline (CPIP), 2-(4-bromophenyl)imidazo[4,5-f][1,10]phenan

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42

Deady, LW, and EH Kachab. "A Synthesis of 1-Methoxyisoquinoline-3,4-Diamine and Some Derived Imidazo[4,5-C]Isoquinolines." Australian Journal of Chemistry 39, no. 12 (1986): 2089. http://dx.doi.org/10.1071/ch9862089.

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A convenient synthesis of 1-methoxyisoquinoline-3,4-diamine is described. From this, one-carbon bridging units were used to prepare the angular imidazo [4,5-c] isoquinoline system containing 2-aryl, 2-thio and 2-amino substituents . From the latter two, further ring formation between substituent and imidazo nitrogen was investigated.

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Dhanalakshmi, G., Mala Ramanjaneyulu, Sathiah Thennarasu, and S. Aravindhan. "Crystal structure and Hirshfeld surface analysis of two imidazo[1,2-a]pyridine derivatives: N-tert-butyl-2-(4-methoxyphenyl)-5-methylimidazo[1,2-a]pyridin-3-amine and N-tert-butyl-2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridin-3-amine." Acta Crystallographica Section E Crystallographic Communications 74, no. 12 (2018): 1913–18. http://dx.doi.org/10.1107/s2056989018016651.

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In the title imidazo[1,2-a]pyridine derivatives, N-tert-butyl-2-(4-methoxyphenyl)-5-methylimidazo[1,2-a]pyridin-3-amine, C19H23N3O, (I), and N-tert-butyl-2-[4-(dimethylamino)phenyl]imidazo[1,2-a]pyridin-3-amine, C19H24N4, (II), the 4-methoxyphenyl ring in (I) and the 4-(dimethylamino)phenyl ring in (II) are inclined to the respective imidazole rings by 26.69 (9) and 31.35 (10)°. In the crystal of (I), molecules are linked by N—H...N hydrogen bonds, forming chains propagating along the [001] direction. The chains are linked by C—H...π interactions, forming layers parallel to the (010) plane. In

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44

Behera, Santosh Kumar, and G. Krishnamoorthy. "Perturbation of cationic equilibrium by cucurbit-7-uril." Physical Chemistry Chemical Physics 19, no. 29 (2017): 19234–42. http://dx.doi.org/10.1039/c7cp03583g.

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The effect of cucurbit-7-uril (CB-7) on a catonic mixture with the same charge has been investigated by studying monocationic mixtures of 2-(4′-N,N-dimethylaminophenyl)imidazo[4,5-b]pyridine (DMAPIP-b) and 2-(4′-N,N-dimethylaminophenyl)imidazo[4,5-c]pyridine (DMAPIP-c).

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Sun, Shengnan, Hexia Ye, Haibo Liu, Junchen Li та Xiaojing Bi. "Iron-Catalyzed Sulfonylmethylation of Imidazo[1,2-α]pyridines with N,N-Dimethylacetamide and Sodium Sulfinates". Molecules 29, № 13 (2024): 3196. http://dx.doi.org/10.3390/molecules29133196.

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Functionalized imidazo[1,2-α]pyridines are important scaffolds in pharmaceuticals. Herein, we present an efficient 3-sulfonylmethylation protocol for imidazo[1,2-α]pyridines by sodium sulfinates in DMA and H2O (2:1) via an FeCl3-catalyzed three-component coupling reaction. Various sulfonylmethyl imidazo[1,2-α]pyridines were thus afforded in high yields with excellent functional group tolerance. A plausible oxidation-addition mechanism was proposed.

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Böhm, Stanislav, Richard Kubík, Martin Hradilek, et al. "Sterically Crowded Heterocycles. I. Molecular Structure of 3-Chain Substituted 2-Phenylimidazo[1,2-a]pyridinium Salts." Collection of Czechoslovak Chemical Communications 59, no. 12 (1994): 2677–90. http://dx.doi.org/10.1135/cccc19942677.

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2-Phenyl-3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridine (I) was converted to corresponding 1-alkyl-2-phenyl-3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridinium salts III - VI and 2-phenyl- 3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridinium perchlorate (VII). The protonation site is discussed in terms of calculated molecular energies of alternative cations. The X-ray structure analyses of enone I and its quaternary periodide III are reported and compared with the PM3 molecular optimizations. 1H NMR and 13C NMR spectra reveal well changes of molecular structures caused b

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47

Hung, Tran, Nguyen Quan, Hoang Van Dong, et al. "Synthesis of 5-Aryl-5H-pyrido[2',1':2,3]imidazo[4,5-b]indoles by Domino Pd- and Cu-Catalyzed C–N Coupling Reactions." Synlett 30, no. 03 (2019): 303–6. http://dx.doi.org/10.1055/s-0037-1611957.

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A series of 5-aryl-5H-pyrido[2',1':2,3]imidazo[4,5-b]indoles was successfully prepared in good yields by a practical four-step strategy. In this procedure, the key step was demonstrated to be the domino Pd-and Cu-catalyzed C–N coupling reactions of 3-bromo-2-(2-bromophenyl)imidazo[1,2-a]pyridine with amines.

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Barlin, GB, LP Davies, B. Glenn, PW Harrison, and SJ Ireland. "Imidazo[1,2-b]pyridazines. XV. Synthesis and Anxiolytic Activity of Some 3-(Benzamidomethyl and fluorobenzamidomethyl)-6-(fluoro, chloro and methylthio)-2-(4-tolyl and 3,4-methylenedioxyphenyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 47, no. 4 (1994): 609. http://dx.doi.org/10.1071/ch9940609.

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Syntheses are reported for some 3-( benzamido-and fluorobenzamido -methyl)-6-( fluoro , chloro and methylthio )-2(4-methyl-, 4-t-butyl-, 4-cyclohexyl- and 3,4-methylenedioxy-phenyl) imidazo-[1,2-b] pyridazines from the relevant 3-unsubstituted imidazo [1,2-b] pyridazines and the N-( hydroxymethyl ) benzamides. In tests of the ability of these compounds to displace [3H]diazepam from rat brain membrane, 3-(3- or 4-fluorobenzamidomethyl)-2-(3,4-methylenedioxyphenyl)-6-methylthioimidazo[1,2-b]- pyridazine bound most strongly, with IC50 2nM; but in behavioural tests in rats the most active compound

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Barlin, GB, LP Davies, and PW Harrison. "Imidazo[1,2-b]Pyridazines. XVIII. Syntheses and Central Nervous System Activities of Some 6-, 7- and 8-(Chloro and methoxy)imidazo[1,2-a]pyridine Analogs." Australian Journal of Chemistry 48, no. 5 (1995): 1031. http://dx.doi.org/10.1071/ch9951031.

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Syntheses are reported for some 2-aryl-3-(benzamidomethyl and methoxy)-6(7 and 8)-chloro- and 6(and 8)-methoxy-imidazo[1,2-a]pyridines. In tests of the ability of these compounds to displace [3H]diazepam from rat brain membrane, those with 6-chloro and 6-methoxy groups bound most strongly, and relatively small differences only were observed between corresponding imidazo[1,2-a]pyridines and imidazo[1,2-b]pyridazines.

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Kubík, Richard, Stanislav Böhm, Iveta Ruppertová, and Josef Kuthan. "Sterically Crowded Heterocycles. III. A General Approach to Imidazo[1,2-a]pyridines by Ferricyanide Oxidation of Quaternary Pyridinium Salts." Collection of Czechoslovak Chemical Communications 61, no. 1 (1996): 126–38. http://dx.doi.org/10.1135/cccc19960126.

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Substituted 1-(pyridin-2-yl)-2,4,6-triphenylpyridinium perchlorates 1b-1e were converted with potassium ferricyanide and potassium hydroxide to sterically crowded 2-phenyl-3-[(Z)-1,3-diphenyl-3-oxopropenyl]imidazo[1,2-a]pyridines 2b-2e accompanied by minor isomeric 2-benzoyl-3,5-diphenyl-1-(pyridin-2-yl)pyrroles 3c-3e. 4-Phenyl-2,6-di(4-substituted phenyl)-1-(pyridin-2-yl)pyridinium salts 4a, 4b gave exclusively corresponding imidazo[1,2-a]pyridines 5a, 5b while the ferricyanide oxidation of 1-(5-iodo- and 5-cyanopyridin-2-yl)-2,4,6-triphenylpyridinium perchlorates 6a, 6b led to mixtures of ma

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