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Journal articles on the topic 'Imidazo[1'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 July 2025

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1

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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2

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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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

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

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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6

Grünefeld, Kunick, and Jones. "1-(Imidazo[1,2-a]pyridin-1-ium-1-yl)-2,3,4-trioxocyclobutan-1-ide." Molbank 2019, no. 3 (2019): M1072. http://dx.doi.org/10.3390/m1072.

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7

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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8

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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9

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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10

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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11

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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12

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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13

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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14

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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15

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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16

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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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

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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19

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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20

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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21

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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22

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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Natarajan, Senthilkumar, and Dominic Ravichandran Yesudass. "Synthesis and study the anti-proliferative effect of new series of 1H-imidazo[4,5-c]quinoline derivatives in MCF-7 (human breast cancer) cells." Journal of Indian Chemical Society Vol. 92, Jun 2015 (2015): 921–24. https://doi.org/10.5281/zenodo.5637681.

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Organic Chemistry Division, School of Advanced Sciences, VIT University, Vellore-632 014, Tamilnadu, India <em>E-mail</em> : dominic.y@vit.ac.in New series of 2-(4-(7-fluoro-8-aryl-1<em>H</em>-imidazo[4,5-c]quinolin-1-yl)phenyl)acetonitrile derivatives of biological interest have been synthesized from commercially available 2-amino-5-bromo-4-fluorobenzoicacid with good yield (70%). Compounds 2-(4-(7-fluoro-8-phenyl-1<em>H</em>-imidazo[4,5-c]quinolin-1-yl)phenyl)acetonitrile (7a) and 2-(4-(7-fluoro-8-(4- iodophenyl)-1<em>H</em>-imidazo[4,5-c]quinolin-1-yl)phenyl)acetonitrile (7b) were also scre

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24

Al-Abboodi1, Doaa Hashim, and Naeemah Al-lami. "NEW METHDOLOGY OF SYNTHESIS PYRAZOLO- THIAZOLO DERIVATIVES WITH STUDY ANTIMICROBAL ACTIVITIES." iraqi journal of market research and consumer protection 16, no. 1 (2024): 1–12. http://dx.doi.org/10.28936/jmracpc16.1.2024.(1).

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In this contribution, new derivatives of thiosemicarbazon, cyclic thiazolidinone, yilidine thiazolidinone, and parazolo-thiazole were synthesized, starting from the reaction of 2 -aminobenzothiazole with p-bromo phenacyl bromide to give the first step of 2(4-bromo phenyl) imidazole (2,1 -b) benzo thiazole (1). Compound (1) then was subjected under Viels Myer Haack to yield 3-carbaldehyde linking with imidazo-benzothiazol (2). Compound (2) condensed with thiosemicarbazide togivenewsynthesis of thiosemicarbazon derivative (3). Compound 4-Oxo-1,3-thiazolidine (4) was constituted from reacting com

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25

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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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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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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28

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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29

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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30

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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31

Kouassi, Francesco Adingra, Coulibaly Souleymane, Tchambaga Etienne Camara, Sioménan Coulibali, Ané Adjou, and Sissouma Drissa. "Synthesis and Evaluation of the Antibacterial Activity of New Imidazo[1,2-a]pyridine- Chalcones Derivatives." Pharmaceutical and Chemical Journal 9, no. 4 (2022): 44–51. https://doi.org/10.5281/zenodo.13973094.

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Numerous studies have shown that conjugated imidazo[1,2-a]pyridine derivatives possess various kinds of biological activities, including antibacterial properties. In this work, we designed and synthesized fifteen (15) imidazo[1,2-a]pyridine-chalcone derivatives (<strong>4a-o</strong>) and studied their antibacterial activity. These compounds were obtained by Claisen-Schmidt condensation between imidazo[1,2-a]pyridine-3-carbaldehyde derivatives (<strong>2a-b</strong> and <strong>3</strong>) and acetophenone derivatives in the presence of sodium hydroxide (NaOH). The synthesized compounds were c

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32

Hannah, Duncan R., and Malcolm F. G. Stevens. "Structural Studies on Bioactive Compounds. Part 38.1 Reactions of 5-Aminoimidazole-4-Carboxamide: Synthesis of Imidazo[1,5-a]Quinazoline-3-Carboxamides." Journal of Chemical Research 2003, no. 7 (2003): 398–401. http://dx.doi.org/10.3184/030823403103174533.

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5-Aminoimidazole-4-carboxamide reacts with aromatic aldehydes to afford Schiff bases which can be cyclised to imidazo[1,5- a]quinazoline-3-carboxamides in DMF/sodium hydride. The potassium salt of imidazo[1,5- a]quinazoline-3-carboxylic acid undergoes deuterium exchange in D2O at the 1-position.

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33

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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34

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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35

Abignente, E., F. Arena, E. Luraschi, et al. "P95 heterocyclic antiinflammatory agents: Imidazo[1,2-1]pyramidines." European Journal of Pharmaceutical Sciences 2, no. 1-2 (1994): 142. http://dx.doi.org/10.1016/0928-0987(94)90268-2.

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36

Bori, Jugal, Nibedita Behera, Satyajit Mahata, and Vadivelu Manivannan. "Synthesis of Imidazo[5, 1-a ]isoquinoline and Its 3-Substituted Analogues Including the Fluorescent 3-(1-Isoquinolinyl)imidazo[5, 1-a ]isoquinoline." ChemistrySelect 2, no. 35 (2017): 11727–31. http://dx.doi.org/10.1002/slct.201702420.

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37

Matschay, A., D. Skwarski, and S. Sobiak. "ChemInform Abstract: Synthesis of 2-(1-Adamantyl)imidazo[1,2-a]pyridine and 2-(1-Adamantyl)imidazo[1,2-a]pyrimidine Derivatives." ChemInform 32, no. 12 (2001): no. http://dx.doi.org/10.1002/chin.200112155.

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38

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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39

Conboy, Darren, and Fawaz Aldabbagh. "6-Imino-1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1′,2′:1,2]imidazo[4,5-f]benzimidazole-13-one: Synthesis and Cytotoxicity Evaluation." Molbank 2020, no. 1 (2020): M1118. http://dx.doi.org/10.3390/m1118.

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The first report of an iminoquinone of imidazo[4,5-f]benzimidazole is described. The 2D-NOESY spectrum of 1,2,3,4,8,9,10,11-octahydropyrido[1,2-a]pyrido[1’,2’:1,2]imidazo[4,5-f]benzimidazol-6-amine was used to confirm the location of the imine moiety at the C-6 position of the title compound. Cytotoxicity data from the National Cancer Institute are included.

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40

Jyothi, Boggavarapu, and Nannapaneni Madhavi. "Green Synthesis and Antimicrobial Activity of Some Novel N-Arylimidazo[1,2-a]pyrazine-2-Carboxamide Derivatives." Asian Journal of Chemistry 32, no. 1 (2019): 84–90. http://dx.doi.org/10.14233/ajchem.2020.22365.

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The article deals with the synthesis of some novel N-arylimidazo[1,2-a]pyrazine-2-carboxamides (7a-l) by condensation reaction of imidazo[1,2-a]pyrazine-2-carboxylic acid (5) with different aliphatic/aromatic amines (6a-l) by using 1-methylimidazole, Mukaiyama’s reagent and 2-chloro-1-methylpyridinium iodide under microwave irradiation conditions. A new series of compounds 7 have been prepared from 2-iodopyrazine (1). Compound 1 on purged with ammonia gas in the presence of Cu2O and K2CO3 furnishes pyrazin-2-amine (2), which is treated with ethyl 3-bromo-2-oxopropanoate (3) to produce ethyl im

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41

Kutschy, Peter, Mojmír Suchý, Milan Dzurilla, Mitsuo Takasugi, and Vladimír Kováčik. "A New Approach to Imidazo[1,5-a]indole Derivatives." Collection of Czechoslovak Chemical Communications 65, no. 7 (2000): 1163–72. http://dx.doi.org/10.1135/cccc20001163.

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Reaction of indole-2-carbonyl isothiocyanate (1) with sodium methanethiolate afforded 1-thioxo-1H-imidazo[1,5-a]indol-3(2H)-one (3). Its methylation with methyl iodide in the presence of lithium hydride in dimethylformamide, or potassium carbonate in acetone resulted in the formation of corresponding S- and N-methyl derivatives 4 and 5. N-(Indole-2-carbonyl)thiocarbamates and N-(indole-2-carbonyl)thioureas prepared by treatment of isothiocyanate 1 with corresponding nucleophilic reagents were S-methylated with methyl iodide in acetone in the presence of potassium carbonate. The obtained N-(ind

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42

El-Abadelah, Mustafa M., Firas F. Awwadi, Ahmad H. Abdullah, and Wolfgang Voelter. "The reaction of imidazo[1,5-a]pyridines with ninhydrin revisited." Zeitschrift für Naturforschung B 75, no. 6-7 (2020): 559–65. http://dx.doi.org/10.1515/znb-2020-0027.

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AbstractThe synthesis of 2,2′-(Imidazo[1,5-a]pyridine-1,3-diyl)bis(2-hydroxy-1H-indene-1,3(2H)-dione) (11) is achieved by reaction of imidazo[1,5-a]pyridine (7) with two equivalents of ninhydrin (1) at room temperature. The structure of this new 1,3-bis-adduct 11 is evidenced from HRMS and NMR spectral data and confirmed by single-crystal X-ray crystallography. Employment of equimolar amounts of 1 and 7 gave a separable mixture of the respective 1- and 3-monomeric adducts (9, 10).

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43

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

Tber, Zahira, Mohammed Loubidi, Jabrane Jouha, et al. "Pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5-amines as Potential Cytotoxic Agents against Human Neuroblastoma." Pharmaceuticals 14, no. 8 (2021): 750. http://dx.doi.org/10.3390/ph14080750.

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We report herein the evaluation of various pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5-amines as potential cytotoxic agents. These molecules were obtained by developing the multicomponent Groebke–Blackburn–Bienaymé reaction to yield various pyrido[2′,1′:2,3]imidazo[4,5-c]quinolines which are isosteres of ellipticine whose biological activities are well established. To evaluate the anticancer potential of these pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5-amine derivatives in the human neuroblastoma cell line, the cytotoxicity was examined using the WST-1 assay after 72 h drug exposure. A clon

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45

Plutecka, Agnieszka, Marcin Hoffmann, Urszula Rychlewska, Zdzisław Kucybała, Jerzy Pączkowski, and Ilona Pyszka. "Relationship between structure and photoinitiating abilities of selected bromide salts of 2-oxo-2,3-dihydro-1H-imidazo[1,2-a]pyridine (IMP): influence of the solvent and the substitution in benzaldehyde on the course of its reaction with IMP." Acta Crystallographica Section B Structural Science 62, no. 1 (2006): 135–42. http://dx.doi.org/10.1107/s0108768105033884.

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2-Oxo-2,3-dihydro-1H-imidazo[1,2-a]pyridinium bromide and its C3-substituted derivatives have been synthesized and structurally characterized by X-ray crystallography and quantum chemical calculations. Their potential as photoinitiators for free-radical polymerization has been investigated experimentally and compared with theoretical results. It has been established that the course of the reaction that introduces the substituted benzylidene group to the imidazole ring is different in the protic and dipolar aprotic solvents, and also depends on the character of the substituent, as the energy ch

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46

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

Sammor, Mervat S., Mustafa M. El-Abadelah, Ahmad Q. Hussein, Firas F. Awwadi, Salim S. Sabri, and Wolfgang Voelter. "A study on the reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines with ninhydrin." Zeitschrift für Naturforschung B 73, no. 6 (2018): 413–21. http://dx.doi.org/10.1515/znb-2018-0039.

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AbstractThe reaction of 3-alkyl(aryl)imidazo[1,5-a]pyridines (1) with ninhydrin in dichloromethane at room temperature delivered good yields of the respective 2-hydroxy-2-(imidazo[1,5-a]pyridine-1-yl)indene-1,3-diones. In the presence of dimethyl acetylenedicarboxylate (DMAD), this uncatalyzed electrophilic substitution reaction, involving C-1 (in 1) and the central C=O (in ninhydrin), takes precedence over the three-component 1,4-dipolar cycloaddition reaction. This selectivity is probably due to the higher electrophilicity of the carbonyl carbon-2 in ninhydrin as compared to that of the sp-c

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48

Abe, Noritaka, Hiroyuki Fujii, Akikazu Kakehi, and Motoo Shiro. "Revised Structures, 1-Methylene-1H-[1,4]thiazino[4,3-a]-benzimidazole and 10-Methylene-10H-imidazo[2,1-c][1,4]-benzothiazine Derivatives, for the Cycloadducts Accompanying Rearrangement from Imidazo[2,1-b]benzothiazole and Thiazolo [3,2-a] benzimidazole Derivatives with Propiolic Esters." Journal of Chemical Research 23, no. 5 (1999): 322–23. http://dx.doi.org/10.1177/174751989902300513.

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Formerly-proposed structures, thiazolo[3,2- a] [1,5]benzodiazepine and [1,4]diazepino[7,1- b]benzothiazole derivatives, cycloadducts from the reactions of thiazolo[3,2- a] benzimidazole and imidazo[2,1- b]benzothiazole derivatives with propiolic esters, are revised to methyl 2-[4-methyl-( E)-1 H-[1,4]thiazino[4,3- a]benzimidazol-1-ylidene)methoxycarbonylmethyl]-( E)-acrylate and methyl [2-methyl-( E)-10 H-imidazo[2,1- c] [1,4]benzothiazine-10-ylidene)-methoxycarbonylmethyl]-( E)-acrylate, respectively, whose structures are deduced by X-ray structure analysis.

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49

Izmest’ev, Alexei N., Valentina A. Karnoukhova, Alexander A. Larin, Angelina N. Kravchenko, Leonid L. Fershtat, and Galina A. Gazieva. "Synthesis, Structure and Stereochemistry of Dispirocompounds Based on Imidazothiazolotriazine and Pyrrolidineoxindole." International Journal of Molecular Sciences 23, no. 22 (2022): 13820. http://dx.doi.org/10.3390/ijms232213820.

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Methods for the synthesis of two types of isomeric dispirocompounds based on imidazothiazolotriazine and pyrrolidineoxindole, differing in the structure of imidazothiazolotriazine fragment, namely, linear dispiro[imidazo[4,5-e]thiazolo[3,2-b][1,2,4]triazine-6,3′-pyrrolidine- 4′,3″-indolines] and angular dispiro[imidazo[4,5-e]thiazolo[2,3-c][1,2,4]triazine-7,3′-pyrrolidine-4′,3″-indolines] were proposed. The first method relies on a 1,3-dipolar cycloaddition of azomethine ylides generated in situ from paraformaldehyde and N-alkylglycine derivatives to the corresponding oxindolylidene derivative

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50

Wu, Jiang-Ping, Jonathan Emeigh, Donghong A. Gao та ін. "Second-Generation Lymphocyte Function-Associated Antigen-1 Inhibitors: 1H-Imidazo[1,2-α]imidazol-2-one Derivatives". Journal of Medicinal Chemistry 47, № 22 (2004): 5356–66. http://dx.doi.org/10.1021/jm049657b.

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