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Journal articles on the topic 'Imidazo'

Author: Grafiati

Published: 24 April 2022

Last updated: 26 July 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

Demchenko, Sergii, Roman Lesyk, Oleh Yadlovskyi, et al. "Synthesis, Antibacterial and Antifungal Activity of New 3-Aryl-5H-pyrrolo[1,2-a]imidazole and 5H-Imidazo[1,2-a]azepine Quaternary Salts." Molecules 26, no. 14 (2021): 4253. http://dx.doi.org/10.3390/molecules26144253.

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A series of novel 3-aryl-5H-pyrrolo[1,2-a]imidazole and 5H-imidazo[1,2-a]azepine quaternary salts were synthesized in 58–85% yields via the reaction of 3-aryl-6, 7-dihydro-5H-pyrrolo[1,2-a]imidazoles or 3-aryl-6,7,8,9-tetrahydro-5H-imidazo[1,2-a]azepines and various alkylating reagents. All compounds were characterized by 1H NMR, 13C NMR, and LC-MS. The conducted screening studies of the in vitro antimicrobial activity of the new quaternary salts derivatives established that 15 of the 18 newly synthesized compounds show antibacterial and antifungal activity. Synthesized 3-(3,4-dichlorohenyl)-1

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4

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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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

Boukhallout, Fath Eddine, Mohamed Dehamchia, Samir Bayou, Chaima Adaika, Abdelhafeez M. A. Mohammed, and Zine Regainia. "Synthesis and biological activity of new imidazo[1,2-c]pyrimidin-5(6H)-one, imidazo[2,1-b]purin-4(5H)-one and imidazo[2,1-i]purine as antioxidant and antibacterial agents." INDIAN JOURNAL OF HETEROCYCLIC CHEMISTRY 34, no. 03 (2024): 421. http://dx.doi.org/10.59467/ijhc.2024.34.421.

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This paper investigates the antioxidant and antibacterial applications of new fusedimidazo[1,2-c]pyrimidin- 5(6H)-one, imidazo[2,1-i]purine,andimidazo[2,1-b]purin-4(5H)-one synthesized by the reaction of a-bromoacetophenone with nucleobases (adenine, guanine, and cytosine). The newly synthesized compounds were structurally confirmed using spectral studies and elemental analysis. All the products were screened for their antioxidant capacity by applying the methods of scavenging free radicals (ABTS and DPPH). The antibacterial activity was examined against three bacterial strains: Pseudomonas ae

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7

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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8

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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9

Loubidi, M., M. Lorion, A. El Hakmaoui, P. Bernard, M. Akssira, and G. Guillaumet. "One-Step Synthesis of 1H-Imidazo[1,5-a]imidazole Scaffolds and Access to their Polyheterocycles." Synthesis 51, no. 21 (2019): 3973–80. http://dx.doi.org/10.1055/s-0039-1690182.

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In this work, we continue our adventure in the chemistry of 5-5 tri-nitrogen bicycles. We disclose herein a one-step reaction to synthesize 1H-imidazo[1,5-a]imidazoles with different substituents introduced through the use of a wide range of aldehydes and isocyanides by using a Groebke–Blackburn–Bienaymé multicomponent reaction. The aim is to build a new library of 1H-imidazo[1,5-a]imidazole scaffolds. This bicycle was then modified to access new nitrogen-containing polycyclic compounds.

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10

Vellakkaran, Mari, Rajaka Lingayya, Bejjanki Naveen Kumar, Kommu Nagaiah, Y. Poornachandra, and C. Ganesh Kumar. "Palladium(0)-catalyzed direct C–H hetero-arylation of 2-arylimidazo [1,2-a]pyridines with (E)-1-(5-bromothiophen-2-yl)-3-arylprop-2-en-1-ones and their anticancer activity." RSC Advances 5, no. 97 (2015): 80057–62. http://dx.doi.org/10.1039/c5ra15078g.

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11

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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12

Prasad, Pratibha, Anirudhdha G. Kalola, and Manish P. Patel. "Microwave assisted one-pot synthetic route to imidazo[1,2-a]pyrimidine derivatives of imidazo/triazole clubbed pyrazole and their pharmacological screening." New Journal of Chemistry 42, no. 15 (2018): 12666–76. http://dx.doi.org/10.1039/c8nj00670a.

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An efficient synthetic microwave-assisted, one-pot three-component condensation route for imidazo[1,2-a]pyrimidine derivatives of imidazole 4/triazole 5 clubbed pyrazole catalysed by ecofriendly base KOH.

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13

Saldaña Arredondo, Cristian, Karla A. González Pérez, Jorge Alejandro Tovar Rosales, and María del Rocío Gámez Montaño. "Síntesis verde de imidazo[2,1-b]tiazoles vía Groebke-Blackburn-Bienaymé asistida por microondas." JÓVENES EN LA CIENCIA 28 (October 2, 2024): 1–7. https://doi.org/10.15174/jc.2024.4314.

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Se sintetizó una serie de imidazo[2,1-b]tiazoles a través de un proceso multicomponente, mediante la reacción Groebke-Blackburn-Bienaymé (GBB) en microondas. Los imidazotiazoles sintetizados contienen en su estructura los núcleos de imidazol y tiazol, los cuales se encuentran presentes en una variedad de compuestos bioactivos y fármacos.

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14

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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15

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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16

Rahimizadeh, Mohammad, Mehdi Pordel, Mehdi Bakavoli, Shima Rezaeian, and Hossein Eshghi. "Synthesis of a new heterocyclic system — Fluoreno[1,2-d]imidazol-10-one." Canadian Journal of Chemistry 87, no. 6 (2009): 724–28. http://dx.doi.org/10.1139/v09-062.

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Synthesis of various substituted fluoreno[1,2-d]imidazol-10-ones (5a–5g) has been accomplished by the cyclization of diazotized 1-substituted 4-benzoyl-5- aminobenzimidazoles (4a–4g). Compounds 4a–4g were prepared by reductive ring opening of 3H-imidazo[4′,5′:3,4]benzo[c]isoxazoles (3a–3g) with zinc dust in EtOH/NaOH solution.

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17

Compernolle, Frans, and Suzanne Toppet. "Synthesis of 1H-imidazo[1,2-a]imidazole." Journal of Heterocyclic Chemistry 23, no. 2 (1986): 541–44. http://dx.doi.org/10.1002/jhet.5570230246.

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18

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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19

Aziz, Jessy, and Sandrine Piguel. "An Update on Direct C–H Bond Functionalization of Nitrogen-Containing Fused Heterocycles." Synthesis 49, no. 20 (2017): 4562–85. http://dx.doi.org/10.1055/s-0036-1590859.

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This report highlights the recent advances in direct C–H bond functionalization of 5,5- and 6,5-fused heterocycles containing at least two nitrogen atoms. Besides C–C bond formation, C–N, C–S, C–P, and C–Si bonds can also be created via a metal-catalyzed process. Some examples, where a C–H functionalization approach was applied for the synthesis of drug candidates, will be presented as well.1 Introduction2 C–H Functionalization Reactions of N-Containing Heterocycles2.1 Imidazo[1,2-a]pyridines2.2 Pyrrolo[1,2-a]pyrazines2.3 Imidazo[1,2-b]pyrazoles2.4 Imidazo[1,2-a]pyrimidines2.5 Imidazo[1,2-a]py

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20

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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21

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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22

Skonieczny, Kamil, Jarosław Jaźwiński, and Daniel Gryko. "The Synthesis of Imidazo[1,2-f]phenanthridines, Phenanthro-[9,10-d]imidazoles, and Phenanthro[9′,10′:4,5]imidazo[1,2-f]-phenanthridines via Intramolecular Oxidative Aromatic Coupling." Synthesis 49, no. 20 (2017): 4651–62. http://dx.doi.org/10.1055/s-0036-1589053.

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A short and efficient access to phenanthro[9,10-d]imidazoles, imidazo[1,2-f]phenanthridines, and phenanthro[9′,10′:4,5]imidazo[1,2-f]phenanthridines was achieved by the action of [bis(trifluoroacetoxy)iodo]benzene (PIFA) on properly substituted tetraaryl-imidazoles. By pre-installing suitable electron-donating groups, it is possible to control the site of intramolecular oxidative aromatic coupling. In particular, by placing 3,4-dimethoxyphenyl and 3-methoxyphenyl moieties in close proximity, it was possible to direct the reaction into forming two biaryl linkages leading eventually to the form

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23

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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24

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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25

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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26

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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Salam, Shahana, and Rakesh Kumar Jat. "Imidazole Phenanthroline Derivatives: A Promising Application in Modern Medicine." Journal of Drug Delivery and Therapeutics 15, no. 6 (2025): 102–10. https://doi.org/10.22270/jddt.v15i6.7230.

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Purpose: The primary objective of this study is to create a new class of imidazole phenanthroline compounds that target the 1,10-phenanthroline core for its antifungal and antibacterial properties. Methods: Commercially available 1,10-phenanthroline (phen) was nitrated with potassium bromide in the presence of sulfuric and nitric acids to get 1,10-phenanthroline-5,6-dione (phendione), an intermediate molecule, which served as the starting compound for the synthesis of 1H-imidazo [4,5-f] [1,10] phenanthroline compounds. This intermediate product was dissolved in glacial acetic acid and then rea

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28

Sonawane, Vikas D., Raghunath B. Bhosale, Gajanan S. Rashinkar, and Kailas D. Kailas D. "GREEN SYNTHESIS AND BIOLOGICAL SCREENING OF IMIDAZO [2,1-B] THIAZOLE PYRIMIDINES AS POTENT ANTI-BACTERIAL AGENTS." YMER Digital 21, no. 07 (2022): 280–95. http://dx.doi.org/10.37896/ymer21.07/21.

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A series of Imidazo[2,1-b]thiazole pyrmidine derivatives (3a-g-) were designed, synthesized from imidazo[2,1-b]thiazole chalcone derivatives. (2a-g) and Urea in PEG-400 and evaluated for their anti-bacterial potency. Characterization of newly synthesized compounds was done using IR and 1H NMR and Mass spectroscopy. Further Imidazo [2,1-b]thiazole pyrimidine derivatives were subjected to check their anti-bacterial activities against four different strains, viz two Gram +ve bacteria Staphylococcus aureus & Bacillus subtilis and two Gram -ve bacteria Escherichia coli & Pseudomonas aerugin

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29

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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30

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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31

Vrban, Lucija, Ingrid Ana Martinac, Marijana Hranjec, et al. "Proton and Metal Dication Affinities of Tetracyclic Imidazo[4,5-b]Pyridine-Based Molecules: Insights from Mass Spectrometry and DFT Analysis." Molecules 30, no. 13 (2025): 2684. https://doi.org/10.3390/molecules30132684.

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The imidazo[4,5-b]pyridine scaffold, a versatile heterocyclic system, is renowned for its biological and chemical significance, yet its coordination chemistry with biologically relevant metal dications remains underexplored. This study investigates the proton and metal dication affinities of twelve tetracyclic organic molecules based on the imidazo[4,5-b]pyridine core, focusing on their interactions with Ca(II), Mg(II), Zn(II), and Cu(II). Employing a dual approach of electrospray ionization mass spectrometry (ESI-MS) and density functional theory (DFT) calculations, we characterized the forma

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32

Gui, Qing-Wen, Hongmei Jiang, Dingyi Guo, et al. "Ultrasound-Promoted and Base-Mediated Regioselective Bromination of Imidazo[1,2-a]pyridines with Pyridinium Tribromide." Synthesis 52, no. 18 (2020): 2713–20. http://dx.doi.org/10.1055/s-0040-1707856.

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By using pyridinium tribromide as the bromo source, an efficient and practical protocol for the synthesis of C3-brominated imidazo[1,2-a]pyridines through ultrasound-promoted and Na2CO3-mediated regioselective bromination of imidazo[1,2-a]pyridines has been developed. This method effectively avoids the use of metal catalysts and harsh reaction conditions, and shows attractive characteristics such as operational simplicity, broad substrate scope with good to excellent yields, ease of scale-up and high energy efficiency.

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33

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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34

Slyvka, N. Yu, L. M. Saliyeva, E. M. Kadykalo, T. P. Bortnik, M. B. Litvinchuk, and M. V. Vovk. "Synthesis and growth regulatory activity of phenoxy substituted (benzo)imidazo[2,1-b][1,3]-thiazines." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 4 (July 2022): 61–68. http://dx.doi.org/10.32434/0321-4095-2022-143-4-61-68.

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A number of new 6-phenoxy-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazines 4a–g and their benzoannelated derivatives 4h–l were synthesized by the interaction of substituted 2-chlorobenzenes with 3-hydroxy(benzo)imidazo[2,1-b][1,3]thiazines in mild reaction conditions with the yields of 62–69%. The structure of the target compounds was proven by the results of 1H NMR and 13C NMR spectrometry and LC-MS. All newly synthesized compounds were studied for the features of the physiological development of seedlings of the dicotyledonous plant Cucumis sativus. According to the results of the experiment, it

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35

Anisimova, V. A., I. E. Tolpygin, and G. S. Borodkin. "Studies of Imidazo[1,2-a]Benzimidazoles 31*. Synthesis of 3-(9H-Imidazo[1,2-a]Benz-Imidazol-3-yl)Acrylic Acids." Chemistry of Heterocyclic Compounds 49, no. 9 (2013): 1285–88. http://dx.doi.org/10.1007/s10593-013-1377-z.

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36

Izmest’ev, Alexei N., Dmitry B. Vinogradov, Natalya G. Kolotyrkina, Angelina N. Kravchenko, and Galina A. Gazieva. "Synthesis of functionalized imidazo[4,5-e]thiazolo[3,2-b]triazines by condensation of imidazo[4,5-e]triazinethiones with DMAD or DEAD and rearrangement to imidazo[4,5-e]thiazolo[2,3-c]triazines." Beilstein Journal of Organic Chemistry 17 (May 14, 2021): 1141–48. http://dx.doi.org/10.3762/bjoc.17.87.

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Two series of functionalized imidazothiazolotriazine derivatives were synthesized via the condensation of imidazo[4,5-e]-1,2,4-triazine-3-thiones with acetylenedicarboxylic acid dimethyl and diethyl esters (DMAD and DEAD) and subsequent base-catalyzed rearrangement of the obtained imidazo[4,5-e]thiazolo[3,2-b]-1,2,4-triazines into regioisomeric imidazo[4,5-e]thiazolo[2,3-c]-1,2,4-triazine derivatives.

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37

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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38

Gao, Juanjuan, Xinlei Fu, Kai Yang, and Zhaowen Liu. "Recent Advances in Visible Light-Induced C-H Functionalization of Imidazo[1,2-a]pyridines." Molecules 30, no. 3 (2025): 607. https://doi.org/10.3390/molecules30030607.

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The imidazo[1,2-a]pyridine skeleton is widely present in many natural products and pharmaceutical agents. Due to its impressive and significant biological activities, such as analgesic, anti-tumor, antiosteoporosis, and anxiolytic properties, the derivatization of imidazo[1,2-a]pyridine skeleton has attracted widespread attention from chemists. In recent years, significant progress has been made in the derivatization of imidazo[1,2-a]pyridines through direct C-H functionalization, especially through visible light induction. This review highlights recent advances in visible light-induced C-H fu

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39

Demchenko, Sergii, Sergii Yarmoluk, Volodymyr Sukhovieiev, Oleksandr Golovchenko, Oleksandr Sukhovieiev, and Anatolii Demchenko. "Syntheses and evaluation of novel 3-hydroxy-1,3-diaryl-2,3,5,6,7,8-hexahydro-imidazo[1,2-a]pyridine-1-ium bromides as potential anticancer agents." Pharmacia 71 (November 27, 2024): 1–10. http://dx.doi.org/10.3897/pharmacia.71.e135992.

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New 3-hydroxy-1,3-diaryl-2,3,5,6,7,8-hexahydro-imidazo[1,2-a]pyridine-1-ium bromides have been designed, synthesized, and characterized by 1Н NMR, 13C NMR, and LCMS. The cyclic structure of the condensation products of aryl-(3,4,5,6-tetahydropyridin-2-yl)amines with α-bromoketones has been proven. It has been shown that heating 3-hydroxy-1,3-bis-(41-methoxyphenyl)-2,3,5,6,7,8-hexahydro-imidazo[1,2-a]pyridine-1-ium bromide in acetic anhydride accompanied by elimination of water to form 1,3-bis-(41-methoxyphenyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-1-ium bromide. Antitumor activity of 1,3-

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40

Demchenko, Sergii, Sergii Yarmoluk, Volodymyr Sukhovieiev, Oleksandr Golovchenko, Oleksandr Sukhovieiev, and Anatolii Demchenko. "Syntheses and evaluation of novel 3-hydroxy-1,3-diaryl-2,3,5,6,7,8-hexahydro-imidazo[1,2-a]pyridine-1-ium bromides as potential anticancer agents." Pharmacia 71 (November 27, 2024): 1–10. https://doi.org/10.3897/pharmacia.71.e135992.

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New 3-hydroxy-1,3-diaryl-2,3,5,6,7,8-hexahydro-imidazo[1,2-a]pyridine-1-ium bromides have been designed, synthesized, and characterized by 1Н NMR, 13C NMR, and LCMS. The cyclic structure of the condensation products of aryl-(3,4,5,6-tetahydropyridin-2-yl)amines with α-bromoketones has been proven. It has been shown that heating 3-hydroxy-1,3-bis-(41-methoxyphenyl)-2,3,5,6,7,8-hexahydro-imidazo[1,2-a]pyridine-1-ium bromide in acetic anhydride accompanied by elimination of water to form 1,3-bis-(41-methoxyphenyl)-5,6,7,8-tetrahydro-imidazo[1,2-a]pyridine-1-ium bromide. Antitumor activity of 1,3-

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41

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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42

Jiao, Yuguo, Edward Valente, Solomon T. Garner, Xiaotang Wang, and Hongtao Yu. "Unexpected thermal rearrangement of N-alkoxycarbonyl imidazole acryl azides to imidazo[1,5-c]pyrimidinone or imidazo[4,5-c]pyridinone." Tetrahedron Letters 43, no. 33 (2002): 5879–81. http://dx.doi.org/10.1016/s0040-4039(02)01174-7.

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43

Joshi, Gaurav, Monika Chauhan, Rakesh Kumar, et al. "Cyclocondensation reactions of an electron deactivated 2-aminophenyl tethered imidazole with mono/1,2-biselectrophiles: synthesis and DFT studies on the rationalisation of imidazo[1,2-a]quinoxaline versus benzo[f]imidazo[1,5-a][1,3,5]triazepine selectivity switches." Organic Chemistry Frontiers 5, no. 24 (2018): 3526–33. http://dx.doi.org/10.1039/c8qo00706c.

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44

Yang, Kai, Cai-Bo Chen, Zhao-Wen Liu, Zhen-Lin Li, Yu Zeng, and Zhao-Yang Wang. "C3-Alkylation of Imidazo[1,2-a]pyridines via Three-Component Aza-Friedel–Crafts Reaction Catalyzed by Y(OTf)3." Molecules 29, no. 15 (2024): 3463. http://dx.doi.org/10.3390/molecules29153463.

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As an important class of nitrogen-containing fused heterocyclic compounds, imidazo[1,2-a]pyridines often exhibit significant biological activities, such as analgesic, anticancer, antiosteoporosis, anxiolytic, etc. Using Y(OTf)3 as a Lewis acid catalyst, a simple and efficient method has been developed for the synthesis of C3-alkylated imidazo[1,2-a]pyridines through the three-component aza-Friedel–Crafts reaction of imidazo[1,2-a]pyridines, aldehydes, and amines in the normal air atmosphere without the protection of inert gas and special requirements for anhydrous and anaerobic conditions. A s

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45

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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46

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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47

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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48

Slyvka, N. Yu, L. M. Saliyeva, M. B. Litvinchuk, A. M. Grozav, N. D. Yakovychuk, and M. V. Vovk. "Regioselective synthesis of new (imidazo[2,1-b] [1,3]-thiazin-6-yl)-1,2,3-triazole-5-carboxylates as potential antimicrobial agents." Voprosy Khimii i Khimicheskoi Tekhnologii, no. 5 (October 2023): 114–22. http://dx.doi.org/10.32434/0321-4095-2023-150-5-114-122.

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The paper presents the results of the study on the interaction of azido(benz)imidazo[2,1-b][1,3]thiazines with acetylene carboxylates under non-catalytic conditions according to Huguesgen. It was established that the [3+2]-cyclocondensation of the specified reagents occurs regioselectively upon heating and without the use of a catalyst with the formation of a 1,4-addition product, alkyl 1-((benzo)imidazo[2,1-b][1,3]thiazine-6-yl)-1H-1,2,3-triazole-5-carboxylates 4a–g, the structure of which was thoroughly proved by the methods of 1H (13C) NMR spectroscopy and chromatography-mass spectrometry.

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49

Chitti, Surendar, Kevin Van Calster, Davie Cappoen, et al. "Design, synthesis and biological evaluation of benzo-[d]-imidazo-[2,1-b]-thiazole and imidazo-[2,1-b]-thiazole carboxamide triazole derivatives as antimycobacterial agents." RSC Advances 12, no. 35 (2022): 22385–401. http://dx.doi.org/10.1039/d2ra03318f.

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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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