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Journal articles on the topic '1H-Imidazo[4'

Author: Grafiati

Published: 5 June 2025

Last updated: 1 August 2025

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1

Sunitha, Ch, and G. Brahmeshwari. "Design and Synthesis of some novel 3-benzylidene-1H-benzo [4,5]imidazo[2,1-c] [1,4]oxazine-1,4(3H)-dione derivatives and evaluation of their biological activity." Research Journal of Chemistry and Environment 25, no. 11 (2021): 157–69. http://dx.doi.org/10.25303/2511rjce157169.

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A novel series of 3-arylbenzylidene-1H-benzo[4,5] imidazo[2,1-c][1,4]oxazine-1,4(3H)-dione (4a-l) was synthesized in moderate to good yields. The structures of the newly synthesized compounds were confirmed by 1H NMR, 13C NMR mass spectrometry and elemental analysis. The synthesized compounds were evaluated for their anti-bacterial and anti-oxidant activities. Among all the derivatives tested, the compound 3-(3,5- dimethoxy benzylidene)-1H-benzo [4,5]imidazo[2,1- c][1,4]oxazine-1,4-(3H)-dione showed more potent activity and 3-(4-methoxybenzylidene)-1H benzo[4,5] imidazo[2,1-c][1,4]oxazine-1,4(

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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

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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4

Shamanth, Sadashivamurthy, Kempegowda Mantelingu, Haruvegowda Kiran Kumar, Hemmige S. Yathirajan, Sabine Foro, and Christopher Glidewell. "Crystal structures of three 6-aryl-2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazoles." Acta Crystallographica Section E Crystallographic Communications 76, no. 1 (2020): 18–24. http://dx.doi.org/10.1107/s2056989019016050.

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Three title compounds, namely, 2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]-6-phenylimidazo[2,1-b][1,3,4]thiadiazole, C26H19ClN4S, (I), 2-(4-chlorobenzyl)-6-(4-fluorophenyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazole, C26H18ClFN4S, (II), and 6-(4-bromophenyl)-2-(4-chlorobenzyl)-5-[(1H-indol-3-yl)methyl]imidazo[2,1-b][1,3,4]thiadiazole, C26H18BrClN4S, (III), have been prepared using a reductive condensation of indole with the corresponding 6-aryl-2-(4-chlorobenzyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehydes (aryl = phenyl, 4-fluorophenyl or 4-bromophenyl), and their crystal

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5

Das, Minati, Mongoli Brahma, Sophy A. Shimray, Francis A. S. Chipem, and G. Krishnamoorthy. "Nanoparticle and surfactant controlled switching between proton transfer and charge transfer reaction coordinates." Physical Chemistry Chemical Physics 24, no. 8 (2022): 4944–56. http://dx.doi.org/10.1039/d1cp02165f.

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6

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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7

Loh, Wan-Sin, Hoong-Kun Fun, Reshma Kayarmar, S. Viveka, and G. K. Nagaraja. "4-Hydrazinyl-1-isobutyl-1H-imidazo[4,5-c]quinoline." Acta Crystallographica Section E Structure Reports Online 67, no. 2 (2011): o406. http://dx.doi.org/10.1107/s1600536811001553.

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8

Fun, Hoong-Kun, Wan-Sin Loh, Dinesha, Reshma Kayarmar, and G. K. Nagaraja. "1-Isobutyl-4-methoxy-1H-imidazo[4,5-c]quinoline." Acta Crystallographica Section E Structure Reports Online 67, no. 9 (2011): o2331. http://dx.doi.org/10.1107/s1600536811031801.

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9

Ma, Ling, Liping Lu, and Miaoli Zhu. "2-(4-Methylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline." Acta Crystallographica Section E Structure Reports Online 67, no. 4 (2011): o864—o865. http://dx.doi.org/10.1107/s1600536811008853.

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10

Glushkov, R. G., N. K. Davydova, and N. B. Marchenko. "Synthesis of 4-methyl-1H-imidazo[4,5-c]quinoline." Chemistry of Heterocyclic Compounds 25, no. 2 (1989): 189–90. http://dx.doi.org/10.1007/bf00479915.

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11

Lv, Ying, and Xiang-Rong Hao. "Crystal structure of a binuclear nickel(II) complex constructed of 1H-imidazo[4,5-f][1,10]phenanthroline and doubly deprotonated benzene-1,3,5-tricarboxylic acid." Acta Crystallographica Section E Crystallographic Communications 71, no. 4 (2015): m95—m96. http://dx.doi.org/10.1107/s205698901500420x.

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The title complex, [Ni2(C9H4O6)2(C13H8N4)2(H2O)4]·2H2O, bis(μ-5-carboxybenzene-1,3-dicarboxylato-κ2O1:O1′)bis[diaqua(1H-imidazo[4,5-f][1,10]phenanthroline-κ2N7,N8)nickel(II)] dihydrate, was obtained under solvothermal conditions by the reaction of benzene-1,3,5-tricarboxylic acid (H3BTC) with Ni(NO3)2in the presence of 1H-imidazo[4,5-f][1,10]phenanthroline (IP). The crystal has triclinic (P-1) symmetry with a centrosymmetric binuclear nickel(II) cluster. The NiIIatom is coordinated by two N atoms from a chelating 1H-imidazo[4,5-f][1,10]phenanthroline ligand, two carboxylate O atoms from two 5-

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12

Tran, Phuong Hoang, Thanh-Phuong Thi Bui, Xuan-Quynh Bach Lam, and Xuan-Trang Thi Nguyen. "Synthesis of benzo[4,5]imidazo[1,2-a]pyrimidines and 2,3-dihydroquinazolin-4(1H)-ones under metal-free and solvent-free conditions for minimizing waste generation." RSC Advances 8, no. 63 (2018): 36392–99. http://dx.doi.org/10.1039/c8ra07256f.

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13

Abdulaeva, Inna A., Kirill P. Birin, Anna A. Sinelshchikova, et al. "Imidazoporphyrins as supramolecular tectons: synthesis and self-assembly of zinc 2-(4-pyridyl)-1H-imidazo[4,5-b]porphyrinate." CrystEngComm 21, no. 9 (2019): 1488–98. http://dx.doi.org/10.1039/c8ce01992d.

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14

Šimo, Ondrej, Alfonz Rybár, and Juraj Alföldi. "Synthesis of 4-Alkyl- or 4-Phenyl-7-methyl-1,2-dihydro-7H-imidazo[1,2,3-cd]purine-6,8-diones." Collection of Czechoslovak Chemical Communications 63, no. 3 (1998): 407–15. http://dx.doi.org/10.1135/cccc19980407.

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New 4-alkyl- or 4-phenyl-7-methyl-1,2-dihydro-7H-imidazo[1,2,3-cd]purine-6,8-diones 1 were obtained by intramolecular alkylation of 8-alkyl- or 8-phenyl-9-(2-mesyloxyethyl)-1-methyl-9H-purine-2,6(1H,3H)-diones 5. The necessary compounds 5 were prepared from 6-[(2-hydroxyethyl)- amino]-3-methyl-5-nitrosopyrimidine-2,4(1H,3H)-dione (2), which was hydrogenated to 5-amino-6-[(2-hydroxyethyl)amino]-3-methyl derivative 3; consecutive reactions of the latter with an orthocarboxylate and mesyl chloride afforded 8-alkyl- or 8-phenyl-9-(2-hydroxyethyl)-1-methyl-9H-purine- 2,6(1H,3H)-diones 4 and compoun

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15

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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16

Singh, Gurvinder Pal, K. Sarvanan, and Gyanendra Kumar Sharma. "Microwave Assisted Synthesis of Some New 2-(4-Substituted phenyl)-3-(1H-indol-4-yl)imidazo[4,5-b]indoles of Biological Interest." Asian Journal of Chemistry 36, no. 12 (2024): 2905–10. https://doi.org/10.14233/ajchem.2024.32760.

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A novel series of imidazo-indole hybrid compounds, focusing on their antibacterial, anticancer and anthelmintic efficacy was designed and synthesized. All the compounds, 2-(4-substituted phenyl)-3-(1H-indol-4-yl)imidazo[4,5-b]indoles (1b-10b) were characterized by FT-IR, 1H NMR, 13C NMR, mass spectrometry and elemental analysis. Conventional heating and microwave irradiation were both used in the synthesis process, although the microwave irradiation provided better efficiency, faster response times and safer environmental conditions. The synthesized compounds were screened for their antibacter

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17

Gad-Elkareem, Mohamed A. M., Azza M. Abdel-Fattah, and Mohamed A. A. Elneairy. "Pyrazolo[3,4-b]pyridine in heterocyclic synthesis: synthesis of new pyrazolo[3,4-b]pyridines, imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines, and pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines." Canadian Journal of Chemistry 85, no. 9 (2007): 592–99. http://dx.doi.org/10.1139/v07-089.

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Pyrazolo[3,4-b]pyridine derivatives 7 and 9 were synthesized via the reaction of 3-amino-1H-pyrazolo-[3,4-b]pyridine derivative 2 with ω-bromoacetophenones. Reaction of 7 and 9 with Ac2O afforded the imidazo[1',2':1,5]py razolo[3,4-b]pyridine derivative 8 and pyrazolo[3,4-b]pyridine derivative 10, respectively. Reaction of 2 with chloroacetonitrile followed by DMF-DMA gave imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines 4 and 5, respectively. Acetyl acetone and 1,1-dicyano-2,2-dimethylthioethene were reacted with 2 to afford the pyrido[2',3':3,4]pyrazolo-[1,5-a]-pyrimidines 11 and 14, respectively.

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18

Yutilov, Yu M., and A. G. Ignatenko. "Quaternization of 1H-imidazo[4,5-b]pyridine and 4-methyl-4H-imidazo[4,5-b]pyridine." Chemistry of Heterocyclic Compounds 30, no. 9 (1994): 1067–68. http://dx.doi.org/10.1007/bf01171166.

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19

Cheng, Jing, Zuming Liu, and Guangfu Yang. "1-(2-Methylpropyl)-1H-imidazo[4,5-c]quinolin-4-amine." Acta Crystallographica Section E Structure Reports Online 61, no. 8 (2005): o2638—o2639. http://dx.doi.org/10.1107/s1600536805022579.

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20

Špirková, Katarína, and Štefan Stankovský. "Annelation to the Quinazoline Ring. Preparation of Some Substituted 2H-Imidazo- and 2,3-Dihydropyrimido[1,2-c]quinazolines." Collection of Czechoslovak Chemical Communications 61, no. 6 (1996): 957–61. http://dx.doi.org/10.1135/cccc19960957.

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Preparation of some substituted 2H-imidazo[1,2-c]quinazolin-3-ones (2a-2f) and 2,3-dihydropyrimido[1,2-c]quinazolin-4-ones (3a-3c) by reaction of corresponding 3H-quinazoline-4-thiones (1a-1d) with amino acid esters is described. IR, 1H NMR and 13C NMR spectra of the compounds synthesized are presented.

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21

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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22

Dzedulionytė, Karolina, Melita Veikšaitė, Vít Morávek, et al. "Convenient Synthesis of N-Heterocycle-Fused Tetrahydro-1,4-Diazepinones." Molecules 27, no. 24 (2022): 8666. http://dx.doi.org/10.3390/molecules27248666.

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A general approach towards the synthesis of tetrahydro-4H-pyrazolo[1,5-a][1,4]diazepin-4-one, tetrahydro[1,4]diazepino[1,2-a]indol-1-one and tetrahydro-1H-benzo[4,5]imidazo[1,2-a][1,4]diazepin-1-one derivatives was introduced. A regioselective strategy was developed for synthesizing ethyl 1-(oxiran-2-ylmethyl)-1H-pyrazole-5-carboxylates from easily accessible 3(5)-aryl- or methyl-1H-pyrazole-5(3)-carboxylates. Obtained intermediates were further treated with amines resulting in oxirane ring-opening and direct cyclisation—yielding target pyrazolo[1,5-a][1,4]diazepin-4-ones. A straightforward tw

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23

Jeyanthi, A., B. Kusuma, and Dayakar Gade. "Synthesis of Diazepine and Thiazepine derivatives of 1H-imidazo [4, 5-b] pyridines (Research Article)." International Journal of Pharmacy and Biological Sciences 11, no. 1 (2021): 87–91. http://dx.doi.org/10.21276/ijpbs.2021.11.1.11.

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24

Kumar, G. Santosh, S. Pushpa Ragini, A. Sanjeeva Kumar, and H. M. Meshram. "A copper-catalyzed multi-component reaction accessing fused imidazo-heterocycles via C–H functionalization." RSC Advances 5, no. 64 (2015): 51576–80. http://dx.doi.org/10.1039/c5ra09025c.

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An efficient synthesis of fused imidazo-heterocycles is described using Cu(OTf)<sub>2</sub> in [bmim]BF<sub>4</sub> by the multi-component reaction of pyridin-2(1H)-one or thiazol/benzo[d]thiazol-2(3H)-ones with O-tosylhydroxyl amine and acetophenones under microwave irradiation.

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25

Loh, Wan-Sin, Hoong-Kun Fun, Reshma Kayarmar, S. Viveka, and G. K. Nagaraja. "4-Chlorobenzaldehyde (1-isobutyl-1H-imidazo[4,5-c]quinolin-4-yl)hydrazone monohydrate." Acta Crystallographica Section E Structure Reports Online 67, no. 2 (2011): o407—o408. http://dx.doi.org/10.1107/s1600536811001577.

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26

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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27

Zheng, Chun-Yang, and Ting-Quan Sun. "2-(4-tert-Butylphenyl)-1H-imidazo[4,5-f][1,10]phenanthroline sesquihydrate." Acta Crystallographica Section E Structure Reports Online 65, no. 7 (2009): o1471. http://dx.doi.org/10.1107/s1600536809020261.

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28

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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29

Podchezertseva, K. V., T. M. Zamaraeva, N. V. Slepova, and M. V. Dmitriev. "Synthesis and Structure of Ethyl 4-Aryl-2-oxo-2,3,4,10-tetrahydrobenzo[4,5]imidazo[1,2-<i>a</i>]pyrimidine-3-carboxylates." Žurnal obŝej himii 94, no. 6 (2024): 699–704. http://dx.doi.org/10.31857/s0044460x24060034.

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Ethyl 4-aryl-2-oxo-2,3,4,10-tetrahydrobenzo[4,5]imidazo[1,2-a]pyrimidine-3-carboxylates were prepared by three-component one-pot condensation of diethylmalonate, aromatic aldehyde, 2-aminobenzimidazole in ethanol in the presence of piperidine. The structure of the obtained compounds was determined by 1H, 13С NMR spectroscopy and single crystal X-ray diffraction analysis.

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30

Balwe, Sandip Gangadhar, and Yeon Tae Jeong. "An approach towards the synthesis of novel fused nitrogen tricyclic heterocyclic scaffolds via GBB reaction." Organic & Biomolecular Chemistry 16, no. 8 (2018): 1287–96. http://dx.doi.org/10.1039/c7ob02933k.

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A concise and efficient one-pot synthesis of novel N-fused tricyclic derivatives has been developed by using the Groebke–Blackburn–Bienaymé (GBB) reaction, which involved the reaction of 3-amino-1H-indazoles, aldehydes and isonitriles to afford 2-aryl-5H-imidazo[1,2-b]indazol-3-amine derivatives via a formal [4 + 1] cycloaddition reaction.

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31

Innes, Dylan, Michael V. Perkins, Andris J. Liepa, and Craig L. Francis. "N,N-Dialkyl-N′-Chlorosulfonyl Chloroformamidines in Heterocyclic Synthesis. Part XIV. Synthesis and Reactivity of the New Benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine Ring System." Australian Journal of Chemistry 71, no. 1 (2018): 58. http://dx.doi.org/10.1071/ch17255.

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N,N-Dialkyl-N′-chlorosulfonyl chloroformamidines 1 underwent regioselective reactions with the 1,3-NCC bis-nucleophilic 1H-benzimidazole-2-acetonitriles 4 and related compounds to produce benzo[4,5]imidazo[1,2-b][1,2,6]thiadiazine dioxides 6, 9, 12, and 14, representatives of a new ring system. Reaction of dichlorides 1 with trifluoroacetyl derivative 16 afforded benzo[4,5]imidazo[1,2-c]pyrimidines 19 and 20. An N-acyl and some N-alkyl derivatives of benzimidazo-thiadiazines 6 were prepared to demonstrate the potential of this new ring system as a novel scaffold for synthetic and medicinal che

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32

Sun, Jing, Wen-Xiu Chen, Xing-Dong Song, et al. "Synthesis, Characterization, and Inducing Tumor Cell Apoptosis of Two Ru(II) Complexes Containing Guanidinium as Ligands." Anti-Cancer Agents in Medicinal Chemistry 18, no. 1 (2018): 110–20. http://dx.doi.org/10.2174/1871520617666170419122056.

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Description: Two new ruthenium(II) complexes containing guanidinium as ligands, [Ru(dip)2 (L1)]3+ (Ru1) and [Ru(dip)2(L2)]3+ (Ru2) (dip=4,7-diphenyl-1,10-phenanthroline; L1=1-(4-(1H-imidazo[4,5- f][1,10]phenanthrolin-2-yl)phenyl)guanidine cation; L2 = 1-(3-(1H-imidazo[4,5-f][1,10]phenanthrolin-2-yl) phenyl)guanidine cation) have been synthesized and characterized. Both complexes display higher cytotoxicity against several cancer cell lines compared to cisplatin and are less cytotoxic on the nontumorigenic cell line LO2. Intracellular distribution studies show that these complexes are selective

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33

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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34

Deady, LW, PM Loria, and NH Quazi. "Fused Isoquinoline Systems From Reactions of an Iminoisocoumarin With Nitrogen Nucleophiles." Australian Journal of Chemistry 49, no. 4 (1996): 485. http://dx.doi.org/10.1071/ch9960485.

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Some reactions of 1-acetylimino-3-methyl-1H-2-benzopyran-4-carbonitrile with nitrogen nucleophiles are reported. This is a versatile intermediate and leads to isoquino [1,2-b] quinazoline (with methyl anthranilate ), [1,2,4] triazolo [5,1-a] isoquinoline (with hydrazine), imidazo [2,1-a] isoquinoline (with glycine ethyl ester), benzimidazo [2,1-a] isoqinoline (with o-phenylenediamine) and 1,3,5-triacine (with acetamidine ) systems.

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35

Izumi, Tomoyuki, Jun Sakaguchi, Makoto Takeshita та ін. "1H-Imidazo[4,5-c]quinoline derivatives as novel potent TNF-α suppressors: synthesis and structure–activity relationship of 1-, 2-and 4-substituted 1H-imidazo[4,5-c]quinolines or 1H-imidazo[4,5-c]pyridines". Bioorganic & Medicinal Chemistry 11, № 12 (2003): 2541–50. http://dx.doi.org/10.1016/s0968-0896(03)00178-0.

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36

Shablykin, O. V., S. A. Chumachenko, and V. S. Brovarets. "Reactions of New N-(2,2-Dichloro-1-cyanoethenyl)amides with Aliphatic Amines." Russian Journal of General Chemistry 91, no. 9 (2021): 1607–12. http://dx.doi.org/10.1134/s1070363221090012.

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Abstract The reaction of the newly synthesized N-(2,2-dichloro-1-cyanoethenyl)prop-2-enamide and 4-chloro-N-(2,2-dichloro-1-cyanoethenyl)butanamide with methylamine or dimethylamine gave rise to previously unknown 5-amino-1,3-oxazole-4-carbonitriles. In the case of the reaction of N-(2,2-dichloro-1-cyanoethenyl)amides with ethylenediamine diacetate, new (Z)-2,3,5,6,7,8-hexahydro-7-oxo-1H-imidazo[1,2-a][1,4]diazepine-9-carbonitrile and 4-chloro-N-(cyano(imidazolidin-2-ylidene)methyl)butanamide were obtained.

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37

Abou-Hadeed, Khaled, and Wolfgang Pfleiderer. "Synthesis and Properties of Condensed Lumazine-Ringsystems." Pteridines 13, no. 3 (2002): 65–72. http://dx.doi.org/10.1515/pteridines.2002.13.3.65.

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Abstract 1,3-Dimethyllumazine-6,7-diamine (1) and its monomethyl -(3,4) and monophenylamino (5) derivates are interesting starting materials for the synthesis of imidazo[4,5-g] (6-22) and pyrazino[2,3-g]lumazines (23-26). Ringclosure proceeds under relative drastic conditions and the resulting reaction products are highly fluorescent. Methylation of 5,7-dimethyll-imidazo[4,5-g)lumazine (6) led to an isomeric mixture of the 1- (17) and 3-methyl derivatives (7) which could be separated chromatographically. Their structural assignment was based on unambiguous syntheses heating 4 and 3, respective

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38

Loh, Wan-Sin, Hoong-Kun Fun, Reshma Kayarmar, S. Viveka, and G. K. Nagaraja. "1-Isobutyl-N,N-dimethyl-1H-imidazo[4,5-c]quinolin-4-amine." Acta Crystallographica Section E Structure Reports Online 67, no. 2 (2011): o405. http://dx.doi.org/10.1107/s160053681100153x.

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39

Rosepriya, S., M. Venkatesh Perumal, A. Thiruvalluvar, et al. "2-(4-Fluorophenyl)-1-phenyl-1H-imidazo[4,5-f][1,10]phenanthroline monohydrate." Acta Crystallographica Section E Structure Reports Online 67, no. 8 (2011): o1965. http://dx.doi.org/10.1107/s1600536811026328.

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40

Van Galen, Philip J. M., Peter Nissen, Ineke Van Wijngaarden, Adriaan P. Ijzerman, and Willem Soudijn. "1H-Imidazo[4,5-c]quinolin-4-amines: novel non-xanthine adenosine antagonists." Journal of Medicinal Chemistry 34, no. 3 (1991): 1202–6. http://dx.doi.org/10.1021/jm00107a046.

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41

Slyvka, Nataliia, Lesya Saliyeva, Mariia Litvinchuk, Alina Grozav, Nina Yakovychuk та Mykhailo Vovk. "Synthesis, Аntibacterial, Аntifungal, and Antioxidant Activity of New (Benzo)Imidazo[2,1-b][1,3]Thiazine Quaternary Salts". Chemistry & Chemical Technology 19, № 2 (2025): 242–49. https://doi.org/10.23939/chcht19.02.242.

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A series of quaternary salts – 1-phenacyl(4-chlorophenacyl)-6-hydroxy-6,7-dihydro-5H-benzo[4,5]imidazo[2,1-b][1,3]thiazinium bromides 4a-f were obtained. Their structures were rigorously proven by the methods of 1H NMR, 13C NMR spectroscopy, and chromatography-mass spectrometry. All obtained compounds were tested in in vitro experiments for antibacterial, antifungal, and antioxidant activity. Bioscreening results showed that 1-(4-chlorophenacyl)-6-hydroxy-6,7-dihydro-5H-benzo[4,5]imidazo[2,1-b][1,3]thiazinium bromide 4f exhibits the highest antibacterial activity against the strain of gram-pos

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42

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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43

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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44

Bhuva, V. V., V. N. Bhadani, H. D. Purohit, and Dipak M. Purohit. "Synthesis, Spectral Studies and Biological Screening of 2-(4'-Chlorophenyl)-6-Methyl-(3-N, N’-Diaryl/Dialkyl Amino Methyl)-Imidazo[1,2-a]Pyridine." International Letters of Chemistry, Physics and Astronomy 49 (April 2015): 167–71. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.49.167.

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2-(4'-chlorophenyl)-6-methyl- (3-N, N'- diaryl/dialkyl amino methyl)-imidazo [1, 2-a] pyridine (4a-4l) has been synthesized. The products have been assayed for their biological activity against Gram +ve, Gram –ve bacteria and fungi. Some of the products showed moderate activity in concentration 50μg/ml. The structures of the products have been elucidated by IR, 1H-NMR, Mass spectral data, elemental analysis and thin layer chromatography.

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45

Bhuva, V. V., V. N. Bhadani, H. D. Purohit, and Dipak M. Purohit. "Synthesis, Spectral Studies and Biological Screening of 2-(4'-Chlorophenyl)-6-Methyl-(3-N, N’-Diaryl/Dialkyl Amino Methyl)-Imidazo[1,2-a]Pyridine." International Letters of Chemistry, Physics and Astronomy 49 (April 7, 2015): 167–71. http://dx.doi.org/10.56431/p-26vqfo.

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2-(4'-chlorophenyl)-6-methyl- (3-N, N'- diaryl/dialkyl amino methyl)-imidazo [1, 2-a] pyridine (4a-4l) has been synthesized. The products have been assayed for their biological activity against Gram +ve, Gram –ve bacteria and fungi. Some of the products showed moderate activity in concentration 50μg/ml. The structures of the products have been elucidated by IR, 1H-NMR, Mass spectral data, elemental analysis and thin layer chromatography.

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46

Zhuang, Qiya, Chunmei Li, Qingqing Shao, and Bo Jiang. "5-(4-Fluorophenyl)-2,6-dioxo-2,3,6,7,8,9-hexahydro-1H,5H-imidazo[1,2-a]quinoline-4-carbonitrile." Acta Crystallographica Section E Structure Reports Online 63, no. 10 (2007): o3935. http://dx.doi.org/10.1107/s1600536807042110.

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47

Moohambihai, P., and K. Nagashri. "Synthesis and <i>in vitro</i> Biological Studies of Copper Complexes Derived from Some Novel Hetero-Organoselanylquinoline Ligands." Journal of Scientific Research 14, no. 2 (2022): 641–58. http://dx.doi.org/10.3329/jsr.v14i2.56544.

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A set of copper(II) complexes (3a-i) comprises (16E)-N-(2-phenylquinolin-4(1H)-ylidene)-3-(phenlselanyl)pyridine-2-amine (L1-L3), (16E)-2,6-dimethyl-N-(2-phenylquinolin-4(1H)-ylidene)-5-(phenlselanyl)pyrimidine-4-amine (L4-L6), 16E)-N-(2-phenylquinolin-4(1H)-ylidene)-2-(phenylselanyl)H-imidazo[1,2-α]pyridine-3-amine (L7-L9) ligands were synthesised and characterised using spectroscopic techniques. The metal-to-ligand 1:1 stoichiometry of prepared copper complexes was confirmed by mass spectra. The Cu(II) ion produces complexes with a distorted square planar, according to UV–Vis and ESR spectro

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48

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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49

Bhuva, V. V., V. N. Bhadani, H. D. Purohit, and Dipak M. Purohit. "Synthesis and Antimicrobial Screening of 2"-Amino-4"-[2-(4'-Chlorophenyl)-6-Methyl Imidazo[1, 2-a]Pyridine -3-yl]-6"-Aryl-4"-H-Pyran-3"-Carbonitrile." International Letters of Chemistry, Physics and Astronomy 49 (April 2015): 149–54. http://dx.doi.org/10.18052/www.scipress.com/ilcpa.49.149.

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3-Cyano-4,6-disubstituted 4H-pyrans are endowed with a variety of pharmacodynamic activities Looking to the interesting properties of cyanopyrans, it was considered worthwhile to synthesis some new 2"-amino-4"-[2-(4'-chlorophenyl) -6-methyl imidazo [1,2-a] pyridin-3-yl]-6"-aryl-4"-H-pyran-3"- carbonitrile ( 4a-4l ) have been synthesized. The products have been assayed for their biological activity against Gram +ve, Gram –ve bacteria and fungi. Some of the products showed moderate activity in concentration 50μg/mL. The structures of the products have been elucidated by IR, 1H-NMR, Mass spectral

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50

Bhuva, V. V., V. N. Bhadani, H. D. Purohit, and Dipak M. Purohit. "Synthesis and Antimicrobial Screening of 2"-Amino-4"-[2-(4'-Chlorophenyl)-6-Methyl Imidazo[1, 2-a]Pyridine -3-yl]-6"-Aryl-4"-H-Pyran-3"-Carbonitrile." International Letters of Chemistry, Physics and Astronomy 49 (April 7, 2015): 149–54. http://dx.doi.org/10.56431/p-nhm2l9.

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3-Cyano-4,6-disubstituted 4H-pyrans are endowed with a variety of pharmacodynamic activities Looking to the interesting properties of cyanopyrans, it was considered worthwhile to synthesis some new 2"-amino-4"-[2-(4'-chlorophenyl) -6-methyl imidazo [1,2-a] pyridin-3-yl]-6"-aryl-4"-H-pyran-3"- carbonitrile ( 4a-4l ) have been synthesized. The products have been assayed for their biological activity against Gram +ve, Gram –ve bacteria and fungi. Some of the products showed moderate activity in concentration 50μg/mL. The structures of the products have been elucidated by IR, 1H-NMR, Mass spectral

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