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Journal articles on the topic '5]imidazo[1'

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Published: 4 June 2025

Last updated: 1 August 2025

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1

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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2

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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3

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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4

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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5

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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6

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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7

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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8

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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9

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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10

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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11

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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12

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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13

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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14

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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15

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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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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Hassaneen, Huwaida M. E., Enas M. Awad, and Hamdi M. Hassaneen. "Studies with 6,7-Dimethoxy-3,4-dihydroisoquinolin-1-yl-acetonitrile: Novel Syntheses of 1-Azolyl- and Pyridoisoquinolines." Zeitschrift für Naturforschung B 62, no. 1 (2007): 111–16. http://dx.doi.org/10.1515/znb-2007-0116.

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The reaction of 3,4-dihydroisoquinolin-1-yl-acetonitrile with DMFDMA afforded the enaminonitrile 5. Compound 5 was reacted with 2-aminobenzimidazole to yield 4-amino-3-(dihydroisoquinolin- 1-yl)-benzo[4,5]imidazo[1,2-a]pyrimidine (11) and with acetonitrile derivatives to afford pyrido[2,1- a]isoquinolines (15a - g).

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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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19

Ibrahim, Yusria R. "Synthesis of imidazo- and pyrazolothiadiazoles from dithiobiureas and dimethyl ethynedicarboxylate." Journal of Chemical Research 2009, no. 10 (2009): 602–6. http://dx.doi.org/10.3184/030823409x12510192920270.

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Microwave irradiation of 1-substituted-2, 5-dithiobiureas and 1, 6-disubstituted-2, 5-dithiobiureas with dimethyl ethynedicarboxylate gave methyl 2-{6-oxo-2-(substituted amino)imidazo-[2, 1- b][1, 3, 5]thiadiazol-5(6 H)-ylidene} acetate and methyl 7-oxo-1, 3-bis(substituted imino)-3, 7-dihydro-1 H-pyrazolo[1, 2- c][1, 3, 4]thiadiazole-5-carboxylate. Rationales for these transformations are presented.

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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

Solymár, Magdolna, Márta Palkó, Tamás Martinek, and Ferenc Fülöp. "Synthesis of Imidazo[1′,5′:1,2]pyrido[3,4-b]indole Derivatives." Monatshefte f�r Chemie / Chemical Monthly 133, no. 11 (2002): 1423–30. http://dx.doi.org/10.1007/s007060200114.

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Doğanç, Fatıma, and Ali Hakan Göker. "N-Alkylation of Some Imidazopyridines." Fabad Journal of Pharmaceutical Sciences 50, no. 1 (2025): 15–20. https://doi.org/10.55262/fabadeczacilik.1577453.

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6-Bromo-2-(4-(4-fluorophenoxy)phenyl)-4H-imidazo[4,5-b]pyridine (I) and 2-[4-(4-fluorophenoxy)phenyl]-5H-imidazo[4,5-c]pyridine (III) were prepared by the reaction of 5-bromo-2,3-diaminopyridine and 3,4-diaminopyridine with sodyum metabisulfite adduct of 4-(4-fluorophenoxy)benzaldehyde (1), respectively. Alkylation of these compounds with 1-(chloromethyl)-4-methoxybenzene under basic conditions (K2CO3) in DMF) were formed as mainly N4 regioisomer (II) and N5 regioisomer (IV). Their regioisomeric structures were assigned with 2D-NOESY (Nuclear Overhauser Effect Spectroscopy) spectra.

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23

Girges, Margret Mansour, Mohamed Mahmoud Abou El-Zahab, and Mokhtar Ayad Hanna. "Facile synthesis and biological activity of sulfonate ester-containing imidazolylpyridine, imidazo(4,5-b)pyridine and imidazo(5',1':2,3)imidazo(4,5-b)pyridine derivatives." Collection of Czechoslovak Chemical Communications 54, no. 4 (1989): 1096–103. http://dx.doi.org/10.1135/cccc19891096.

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Different ring systems containing imidazole and/or pyridine moieties and accomodating sulfonate ester moiety in their structure were prepared via ring opening of 2-oxazolin-5-one derivatives under various reaction conditions. The assigned structures for the prepared compounds were established through elemental analysis, spectral data and if possible by alternative synthetic routes. The antimicrobial activity of the synthesized compounds was also investigated.

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24

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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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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LOPEZ-RODRIGUEZ, Maria L., M. Jose MORCILLO, Bellinda BENHAMU, Esther FERNANDEZ, Jorge SERRANO, and Luis ORENSANZ. ".ALPHA.1-Adrenoceptor Reagents. Synthesis of Some 5,6,11,11a-Tetrahydro-1H-imidazo(1',5':1,6)pyrido and 5,6,11,11b-Tetrahydro-1H-imidazo(1',5':1,2)pyrido(3,4-b)indole-1,3(2H)-diones." CHEMICAL & PHARMACEUTICAL BULLETIN 43, no. 6 (1995): 941–46. http://dx.doi.org/10.1248/cpb.43.941.

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Hashmi, Imran Ali, Holger Feist, Manfred Michalik, Helmut Reinke та Klaus Peseke. "Dimethylaminomethylene-α-D-xylo-hept-5-ulofuranurononitrile as Building Block in the Synthesis of ‘Reversed’ C-Nucleoside Analogues". Zeitschrift für Naturforschung B 61, № 3 (2006): 292–300. http://dx.doi.org/10.1515/znb-2006-0309.

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Abstract 3-O-Benzyl-6-deoxy-1,2-O-isopropylidene-6-(dimethylaminomethylene)-α-D-xylo-hept-5-ulofuranurononitrile (1) was reacted with amidinium salts, S-methylisothiouronium sulfate, and guanidinium chloride, respectively, in the presence of bases to furnish the 4-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-4-yl)pyrimidine-5-carbonitriles 2 and the 4-(1,2-O-isopropylidene- α-D-glycero-tetr-3-enofuranos-4-yl)pyrimidine-5-carbonitriles 3, respectively. Treatment of 1 with ethyl 5-aminopyrazole-4-carboxylates yielded the ethyl 7-(3-O-benzyl-1,2-O-isopropylidene- α-D-xylo-tetrofuranos-

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Sowmya, A., G. N. Anil Kumar, Sujeet Kumar, and Subhas S. Karki. "The crystal structure of 6-(4-chlorophenyl)-2-(4-methylbenzyl)imidazo[2,1-b][1,3,4]thiadiazole-5-carbaldehyde." Acta Crystallographica Section E Crystallographic Communications 72, no. 10 (2016): 1460–62. http://dx.doi.org/10.1107/s2056989016014754.

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In the title imidazo[2,1-b][1,3,4]thiadiazole derivative, C19H14ClN3OS, the 4-methylbenzyl and chlorophenyl rings are inclined to the planar imidazo[2,1-b][1,3,4]thiadiazole moiety (r.m.s. deviation = 0.012 Å) by 64.5 (1) and 3.7 (1)°, respectively. The molecular structure is primarily stabilized by a strong intramolecular C—H...O hydrogen bond, leading to the formation of a pseudo-seven-memberedS(7) ring motif, and a short intramolecular C—H...N contact forming anS(5) ring motif. In the crystal, molecules are linked by pairs of C—H...S hydrogen bonds, forming inversion dimers. The dimers are

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29

Tber, Z., M. A. Hiebel, H. Allouchi, et al. "Metal free direct formation of various substituted pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5-amines and their further functionalization." RSC Advances 5, no. 44 (2015): 35201–10. http://dx.doi.org/10.1039/c5ra03703d.

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Original substituted pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5-amines have been easily prepared via an Groebke–Blackburn–Bienaymé MCR, then an N-deprotection followed by a spontaneous final cyclization step.

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30

Ma, Jun, Fumio Yoneda, and Tomohisa Nagamatsu. "Synthesis of 6-Azapurines by Transformation of Toxoflavins and Reumycins (7-Azapteridines) and their Cytotoxicities." Australian Journal of Chemistry 68, no. 2 (2015): 203. http://dx.doi.org/10.1071/ch14425.

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This paper describes a reliable and facile synthesis of 6-azapurines, 1,5-dimethyl-1H-imidazo[4,5-e][1,2,4]triazin-6(5H)-ones and 5-methyl-5H-imidazo[4,5-e][1,2,4]triazin-6(7H)-ones, by treatment of toxoflavins and reumycins with 10 % aqueous or ethanolic sodium hydroxide at 5–70°C or reflux, followed by decarboxylation and oxidation by air along with a benzilic acid type rearrangement. Furthermore, heating the produced 6-azapurines in 10 % ethanolic sodium hydroxide afforded the corresponding 1-methyl-5,6-dioxo-1,4,5,6-tetrahydro-1,2,4-triazines with 1-methylurea. The antitumour activities of

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31

Yagishita, Fumitoshi, Natsumi Kozai, Chiho Nii, et al. "Synthesis of Dimeric Imidazo[1, 5-a ]pyridines and Their Photophysical Properties." ChemistrySelect 2, no. 33 (2017): 10694–98. http://dx.doi.org/10.1002/slct.201702277.

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32

Rao, Achanta Venkata Hanumantha, Rayam Parsharamulu, Malthum Shankaraiah, Vadali Lakshman Rao, and Anireddy Jaya Shree. "Synthesis of Novel 2-Butyl-1H-Benzo [4, 5] Imidazo [1, 2-A] Imidazo [4, 5-E] Pyridine-5-Carbonitrile Derivatives and Evaluation of Their Anticancer Activity." Oriental Journal of Chemistry 32, no. 3 (2016): 1381–87. http://dx.doi.org/10.13005/ojc/320312.

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33

Paolini, John P., Frank P. Palopoli, Louis J. Lendvay, and John Huffman. "Pyrido[2′1′:2,3]imidazo[4,5-c]isoquinoline and the alkylation of pyrido[2′,1′:2,3]imidazo[4,5-c]isoquinolin-5(6H)-one." Journal of Heterocyclic Chemistry 24, no. 3 (1987): 549–53. http://dx.doi.org/10.1002/jhet.5570240303.

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34

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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35

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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36

Saeedi, Shaghayegh, Abbas Rahmati, and Zahra Chavoshpour-Natanzi. "Synthesis of pyrazolo[5′,1′:2,3]imidazo[1,5-c]quinazolin-6(5H)-ones and molecular docking study of their affinity against the COVID-19 main protease." RSC Advances 12, no. 30 (2022): 19579–89. http://dx.doi.org/10.1039/d2ra03179e.

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A novel series of fused pyrazolo[5′,1′:2,3]imidazo[1,5-c]quinazolin-6(5H)-ones were synthesized and their affinity against the COVID-19 main protease was investigated using molecular docking study and compared to that of some used clinical drugs.

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37

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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38

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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39

C., S. ANDOTRA, and SHARMA POONAM. "Synthesis and Antifungal Activity of some Substituted 1,3,4-Oxadiazolo[3,2-a]-s-triazin-5-phenyl-7-thione and Imidazo[2,1-b]-1,3,4-oxadiazol- 5-one." Journal of Indian Chemical Society Vol. 73, Dec 1996 (1996): 702–3. https://doi.org/10.5281/zenodo.5930030.

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Department of Chemistry, University of Jammu, Jammu-180 004 <em>Manuscript received 9 August 1994, revised 3 April 1995, accepted 22 May 1995</em> Synthesis and Antifungal Activity of some Substituted 1 ,3,4-Oxadiazolo[3,2-<em>a</em>]-<em>s</em>-triazin-5-phenyl-7-thione and Imidazo[2,1-<em>b</em>]-1,3,4-oxadiazol- 5-one.

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40

Xiao, Shihua, Zheng Liu, Jinyan Zhao, Meishan Pei, Guangyou Zhang, and Wei He. "A novel fluorescent sensor based on imidazo[1,2-a]pyridine for Zn2+." RSC Advances 6, no. 32 (2016): 27119–25. http://dx.doi.org/10.1039/c6ra01800a.

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41

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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42

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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43

González-Muñiz, Rosario, Natalia De la Figuera, Ma Teresa García-López, and Rosario Herranz. "Unprecedented Base-promoted Oxidation of Imidazo[1',5':1,2]pyrido[3,4-b]indoles." HETEROCYCLES 48, no. 10 (1998): 2061. http://dx.doi.org/10.3987/com-98-8250.

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44

Kalhapure, Vijay, Dhananjay Magar, Nishant Kothalkar, Tushar Khaladkar, and Abhijit Roychowdhury. "Synthesis of Substituted imidazo [1, 5-a] pyrimidine-2-(1H)-one Core Structure." Current Organic Synthesis 17, no. 1 (2020): 23–28. http://dx.doi.org/10.2174/1389200220666191122103445.

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Background and Objective: The objective of our work was to establish a facile and scalable synthesis of imidazopyridone for further use in medicinal chemistry applications. An easy synthesis of a core scaffold will enable the medicinal chemistry community to use imidazopyridone as a privileged scaffold in new chemical entity (NCE) synthesis. Materials and Methods: The synthesis was achieved from commercially available and cheap raw materials like amino acetonitrile hydrochloride or commercially available guanidine. Results: Simple transformation starting from amino acetonitrile hydrochloride l

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45

Akkurt, Mehmet, Sema Öztürk Yıldırım, Fusun Ur, Zafer Cesur, Nesrin Cesur, and Orhan Büyükgüngör. "6-Methyl-N'-(1-methylethylidene)imidazo[2,1-b][1,3]thiazole-5-carbohydrazide monohydrate." Acta Crystallographica Section E Structure Reports Online 61, no. 3 (2005): o718—o720. http://dx.doi.org/10.1107/s160053680500509x.

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46

El Qami, Abdelkarim, Badr Jismy, Mohamed Akssira, Johan Jacquemin, Abdellatif Tikad, and Mohamed Abarbri. "Efficient Synthesis of 1H-Benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-one Derivatives Using Ag2CO3/TFA-Catalyzed 6-endo-dig Cyclization: Reaction Scope and Mechanistic Study." Molecules 28, no. 5 (2023): 2403. http://dx.doi.org/10.3390/molecules28052403.

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A small library of 1H-benzo[4,5]imidazo[1,2-c][1,3]oxazin-1-one derivatives was prepared in good to excellent yields, involving a Ag2CO3/TFA-catalyzed intramolecular oxacyclization of N-Boc-2-alkynylbenzimidazole substrates. In all experiments, the 6-endo-dig cyclization was exclusively achieved since the possible 5-exo-dig heterocycle was not observed, indicating the high regioselectivity of this process. The scope and limitations of the silver catalyzed 6-endo-dig cyclization of N-Boc-2-alkynylbenzimidazoles as substrates, bearing various substituents, were investigated. While ZnCl2 has show

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47

Viktor, Milata, Branislav Pavilek, Dušan Bortňák, Zuzana Svítková, and Michaela Halinkovičová. "Novel synthesis of known carcinogen precursors." Acta Chimica Slovaca 17, no. 1 (2024): 39–44. http://dx.doi.org/10.2478/acs-2024-0005.

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Abstract 5-Amino-1-methylbenzimidazole (2) prepared from 2,4-dinitrochlorobenzene in four steps is a suitable reagent for nucleophilic vinylic substitution with various enolethers (3) thus affording N-substituted enaminoesters — aminoethylene derivatives (4). Their thermal cyclocondensation reaction under the Gould-Jacobs protocol gives regioselectively angularly annelated 8-substituted imidazo[4,5-f]quinolones (5), whose mechanism of origin has been attempted. The obtained results give suitable structures for the synthesis of food-borne carcinogen IQ (1).

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48

Zang, Binbin, та Lihui Wang. "Synthesis and protective effect of pyrazole conjugated imidazo[1,2-a]pyrazine derivatives against acute lung injury in sepsis rats via attenuation of NF-κB, oxidative stress, and apoptosis". Acta Pharmaceutica 73, № 3 (2023): 341–62. http://dx.doi.org/10.2478/acph-2023-0031.

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Abstract The current work was conducted to elucidate the pharmacological effect of pyrazole-conjugated imidazo[1,2-a]pyrazine derivatives against acute lung injury in rats in sepsis and their mechanism of action. Various pyrazole-conjugated imidazo[1,2-a]-pyrazine derivatives have been synthesized in a straightforward synthetic route. They exhibited a diverse range of inhibitory activity against NF-ĸB with IC 50 ranging from 1 to 94 µmol L–1. Among them, compound 3h [(4-(4-((4-hydroxyphenyl)sulfonyl) phenyl)-5-(4-methoxyphenyl)-4,5-dihydro-1H-pyrazol-1-yl) (8-(methylamino)imidazo[1,2-a]pyrazin

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49

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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LOPEZ-RODRIGUEZ, M. L., M. J. MORCILLO, B. BENHAMU, E. FERNANDEZ, J. SERRANO та L. ORENSANZ. "ChemInform Abstract: α1-Adrenoceptor Reagents. Synthesis of Some 5,6,11,11a- Tetrahydro-1H-imidazo(1′,5′:1,6)pyrido and 5,6,11,11b-Tetrahydro-1H- imidazo(1′,5′:1,2)pyrido(3,4-b)indole-1,3(2H)-diones." ChemInform 26, № 48 (2010): no. http://dx.doi.org/10.1002/chin.199548166.

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