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Journal articles on the topic 'Imidazo[2'

Author: Grafiati

Published: 4 June 2021

Last updated: 25 May 2024

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1

Balewski, Łukasz, Franciszek Sączewski, Patrick J. Bednarski, Lisa Wolff, Anna Nadworska, Maria Gdaniec, and Anita Kornicka. "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 (December 14, 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 compounds is determined on a panel of human cancer cell lines, and the relationships between structure and antitumor activity are discussed. The most active 4-chloro-N-(2-(4-chlorophenyl)-7-(4,5-dihydro-1H-imidazol-2-yl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)benzamide (4e) and N-(7-(4,5-dihydro-1H-imidazol-2-yl)-2-(p-tolyl)-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)-[1,1′-biphenyl]-4-sulfonamide (5l) inhibits the growth of the cervical cancer SISO and bladder cancer RT-112 cell lines with IC50 values in the range of 2.38–3.77 μM. Moreover, N-(7-(4,5-dihydro-1H-imidazol-2-yl)-2-phenyl-6,7-dihydro-2H-imidazo[2,1-c][1,2,4]triazol-3(5H)-ylidene)-4-phenoxybenzenesulfonamide (5m) has the best selectivity towards the SISO cell line and induces apoptosis in this cell line.

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2

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

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

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3

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

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

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4

Abdulaeva, Inna A., Kirill P. Birin, Yulia G. Gorbunova, Aslan Yu Tsivadze, and Alla Bessmertnykh-Lemeune. "Post-synthetic methods for functionalization of imidazole-fused porphyrins." Journal of Porphyrins and Phthalocyanines 22, no. 08 (August 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-bromophenyl)-1[Formula: see text]-imidazo[4,5-[Formula: see text]]-5,10,15,20-tetramesitylporphyrin was transformed into useful carboxy- and phosphonato-substituted precursors for material chemistry according to palladium-catalyzed C–C and C–P bond forming reactions.

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5

El Abbouchi, Abdelmoula, Jamal Koubachi, Nabil El Brahmi, and Said El Kazzouli. "Direct arylation and Suzuki-Miyaura coupling of imidazo[1,2-a]pyridines catalyzed by (SIPr)Pd(allyl)Cl complex under microwave-irradiation." Mediterranean Journal of Chemistry 9, no. 5 (November 27, 2019): 347–54. http://dx.doi.org/10.13171/mjc1911271124sek.

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

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6

Cores, Ángel, Mercedes Villacampa, and J. Carlos Menéndez. "2-(3-Bromophenyl)imidazo[2,1-b]oxazole." Molbank 2023, no. 2 (April 4, 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-(3-bromophenacyl)-2-nitroimidazole intermediate could be isolated by reducing the reaction time and was shown to be a precursor of the imidazo[2,1-b]oxazole final product.

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7

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-tetrahydroimidazo [2, 1-b] [1,3] thiazolo [5, 4-d] isoxazole 4a-j. The structures of the new compounds were established by elemental analyses, IR,1H NMR and13C NMR data.

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8

Sadek, Kamal Usef, Afaf Mohamed Abdel-Hameed, Hisham A. Abdelnabi, and Yasser Meleigy. "An efficient green synthesis of novel 1H-imidazo[1,2-a]imidazole-3-amine and imidazo[2,1-c][1,2,4]triazole-5-amine derivatives via Strecker reaction under controlled microwave heating." Green Processing and Synthesis 8, no. 1 (January 28, 2019): 297–301. http://dx.doi.org/10.1515/gps-2018-0093.

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

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9

Tan, Fen, Zheng-Zheng Meng, Xiao-Qin Xiong, Guo-Ping Zeng, and Ming-Wu Ding. "One-Pot Regioselective Synthesis of 2,5,6,7-Tetrahydroimidazo [1,2-a]imidazol-3-ones Starting from (Vinylimino)phosphoranes." Synlett 30, no. 07 (March 26, 2019): 857–59. http://dx.doi.org/10.1055/s-0037-1611760.

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

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10

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

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

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11

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

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

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12

Veltri, Lucia, Bartolo Gabriele, Raffaella Mancuso, Patrizio Russo, Giuseppe Grasso, Corrado Cuocci, and Roberto Romeo. "Palladium-Catalyzed Carbonylative Synthesis of Functionalized Benzimidazopyrimidinones." Synthesis 50, no. 02 (November 23, 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 in the carbonylation step (carried out in the presence of 0.33–1 mol% PdI2 in conjunction with 17–50 mol% KI, at 100 °C and under 20 atm of a 4:1 mixture of CO–air) and the corresponding sodium alkoxide as base in the subsequent isomerization step (carried out in the alcoholic solvent at room temperature). The structures of a representative substrate [N-benzyl-1-(prop-2-yn-1-yl)-1H-benzo[d]imidazol-2-amine] and a representative product [methyl 2-(1-isopentyl-2-oxo-1,2-dihydrobenzo-[4,5]imidazo[1,2-a]pyrimidin-3-yl)acetate] were confirmed by X-ray diffraction analysis.

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13

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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14

Rakhmonov, R., Sh Sharipov, M. Odilzoda, B. Safarov, A. Kobilzoda, and A. Abdurakhmonov. "SYNTHESIS AND FUNCTIONALIZATION OF SOME PARA-R-PHENYLIMIDAZO[2,1-B][1,3,4]- THIADIAZOLE DERIVATIVES." East European Scientific Journal 1, no. 4(68) (May 14, 2021): 54–61. http://dx.doi.org/10.31618/essa.2782-1994.2021.1.68.15.

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

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15

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 (November 21, 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, orthorhombic, space group Pnma), or in analogy with similar reactions, through postulated, but unproven intermediate thiiranium ion 5. Furthermore, in the reaction with 1, 4a prefers isomerization to the N-chloroethyl derivative, 1-chloroethyl-2,3-dihydro-3-methyl-1H-imidazole-2-thione (7), rather than alkylation to 2, while 7 further reacts with 1 to form 3-methyl-1-[(1-methyl-imidazole-2-yl)thioethyl]-1H-imidazole-2-thione (8, monoclinic, space group P 21/c). Additionally, during the isomerization of 3, the postulated intermediate thiiranium ion 5 was not detected by chromatographic and spectroscopic methods, nor by trapping with AgBF4. However, trapping resulted in the formation of the silver complex of compound 3, i.e., bis-{2-[(chloroethyl)thio]-1-methyl-1H-imidazole}-silver(I)tetrafluoroborate (6, monoclinic, space group P 21/c), which cyclized upon heating at 80 °C to 7-methyl-2H, 3H, 7H-imidazo[2,1-b]thiazol-4-ium tetrafluoroborate (4b, monoclinic, space group P 21/c). Finally, we observed thermal isomerization of both 2 and 2,3-dihydro-3-methyl-1-[(1-methyl-1H-imidazole-2-yl)thioethyl]-1H-imidazole-2-thione (8), into 1,2-bis(2,3-dihydro-3-methyl-1H-imidazole-2-thione-1-yl)ethane (9), which confirmed their structures.

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16

Praveen, Aletti S., Hemmige S. Yathirajan, Manpreet Kaur, Badiadka Narayana, Eric C. Hosten, Richard Betz, and Christopher Glidewell. "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 (August 28, 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. The molecular skeletons are all nearly planar and the dihedral angles between the imidazole and aryl rings are 1.51 (8) and 7.28 (8)° in (I), 9.65 (7)° in (II), 10.44 (8)° in (III), and 1.05 (8) and 7.21 (8)° in (IV). The molecules in (I) are linked by three independent C—H...N hydrogen bonds to form ribbons containing alternatingR22(8) andR44(18) rings, and these ribbons are linked into a three-dimensional array by three independent π-stacking interactions. Both (II) and (III) contain centrosymmetric dimers formed by π-stacking interactions but hydrogen bonds are absent, and the molecules of (IV) are linked into centrosymmetricR22(8) dimers by C—H...N hydrogen bonds. Comparisons are made with a number of related compounds.

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17

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 (June 25, 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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18

Shukla, Upendra K., Raieshwar Singh, J. M. Khanna, Anil K. Saxena, Hemant K. Singh, Ravindra N. Sur, Bhola N. Dhawan, and Nitya Anand. "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 activity, the trans-2-[N-(2-hydroxy-1,2,3,4-tetrahydronaphthalene-1-yl)]iminothiazolidine (VIII) has shown marked antidepressant activity, better than imipramine in the tests used, and provides a new structural lead for antidepressants.

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19

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

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

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20

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

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21

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

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22

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

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23

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

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24

Aginagalde, Maialen, Yosu Vara, Ana Arrieta, Ronen Zangi, Vicente L. Cebolla, Arantzazu Delgado-Camón, and Fernando P. Cossío. "Tandem [8 + 2] Cycloaddition−[2 + 6 + 2] Dehydrogenation Reactions Involving Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines." Journal of Organic Chemistry 75, no. 9 (May 7, 2010): 2776–84. http://dx.doi.org/10.1021/jo9022815.

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25

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

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A series of 3-acylaminomethyl-6-(chloro, iodo and methyl)-2-(phenyl, 4′-t-butylphenyl, 4′-cyclohexyl- phenyl, biphenyl-4′-yl, 4′-chlorophenyl and 4′-iodophenyl)imidazo[1,2-b]pyridazines and imidazo[1,2- a]pyridines has been prepared and examined for interaction with central and mitochondrial (peripheral- type) benzodiazepine receptors. The imidazo[1,2-b]pyridazines were generally more selective for the mitochondrial receptors than the corresponding imidazo[1,2-a]pyridines. Of these compounds, 3- acetamidomethyl-2-(biphenyl-4′-yl)-6-chloroimidazo[1,2-b]pyridazine (9) proved to be the most selective in studies of the displacement of [3H]diazepam from peripheral-type and central benzodiazepine receptors (IC50 2·8 nM and 0% displacement at 1000 nM, respectively).

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26

Zhu, Jingyun, Ziyue Chen, Meng He, Daoxin Wang, Liangsen Li, Junchao Qi, Renyi Shi, and Aiwen Lei. "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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27

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

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The syntheses of ethyl {2′-aryl-6′-(chloro, methoxy and unsubstituted)imidazo[1,2-a]pyridin-3′-yl}-2- (acylamino, acetoxy and hydroxy)acetates, 3-benzamidomethyl-2-benzoyl-6-(chloro and methoxy)imidazo-[1,2-a]pyridines, 3-amino-6-chloro-2-phenylimidazo[1,2-a]pyridine and ethyl 2-(2′-phenylimidazo[1,2-a]pyridin-3′-yl)acetate are reported. The ability of these compounds to displace [3H]diazepam from central and mitochondrial (peripheral-type) benzodiazepine receptors has been examined. Ethyl 2-benzamido-2-{6′-chloro-2′-(4′′-chlorophenyl)imidazo[1,2-a]pyridin-3′-yl} acetate (21) was selective for peripheral-type receptors (IC5013 nM) but none bound strongly to central receptors.

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28

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

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The syntheses of some ethyl 2-{2′-aryl-6′-(chloro, iodo and methoxy)imidazo[1,2-b]pyridazin-3′-yl}-2-(acetoxy, acylamino, hydroxy and methoxy)acetates, 6-methyl-2-(p-tolyl)- and 6-chloro-2-(4′-chlorophenyl)-3-trimethylammoniomethylimidazo[1,2-b]pyridazine iodides (and reactions thereof), 2-benzoyl 6-substituted imidazo[1,2-b]pyridazines and 7-(methoxy, chloro and phenylthio)-2-phenylpyrimido-[1,2-b]pyridazin-5-ium-3-olates are reported. The ability of these compounds to displace [3H]diazepam from rat forebrain membrane [central benzodiazepine receptor (BZR)] and rat kidney membrane [mitochondrial (peripheral-type) benzodiazepine receptor (PBR)] has been examined. The most active compound was ethyl 2-{6′-chloro-2′-(p-tolyl)imidazo[1,2-b]pyridazin-3′-yl}-2-hydroxyacetate with IC50 24 nM for displacement from the BZR and 91% displacement at 1000 nM from the PBR; the most selective for the PBR was 6-methyl-3-methylsulfonylmethyl-2-(p-tolyl)imidazo[1,2-b]pyridazine (PBR, IC50 92 nM; BZR, 15% inhibition of binding by [3H]diazepam at 1000 nM).

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29

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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30

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

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31

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 (November 30, 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 (II), the crystal packing also features N—H...N hydrogen bonds, which together with C—H...N hydrogen bonds link molecules to form chains propagating along the c-axis direction. The chains are linked by C—H...π interactions to form layers parallel to the (100) plane. Inversion-related layers are linked by offset π–π interactions [intercentroid distance = 3.577 (1) Å]. The intermolecular interactions of both compounds were analyzed using Hirshfeld surface analysis and two-dimensional fingerprint plots.

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32

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

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The cascade oxidative annulation reactions of aryl imidazolium salts with alkynes proceed efficiently in the presence of [Cp*RhCl₂]₂ and Cu(OAc)₂·H₂O to give substituted imidazo[1,2-a]-quinolinium salts and benzo[ij]imidazo[2,1,5-de]quinolizinium salts.

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33

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 (October 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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34

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

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A series of ruthenium polypyridyl complexes were studied using Raman spectroscopy supported by UV/Vis absorption, luminescence spectroscopy, and luminescence lifetime determination by time-correlated single photon counting (TCSPC). The complexes were characterised to determine the influence of the variation of the conjugation across the main polypyridyl ligand. The systematic and sequential variation of the main polypyridyl ligand, 2-(4-formylphenyl)imidazo[4,5-f][1,10]phenanthroline (FPIP), 2-(4-cyanophenyl)imidazo[4,5-f][1,10]phenanthroline (CPIP), 2-(4-bromophenyl)imidazo[4,5-f][1,10]phenanthroline (BPIP), and 2-(4-nitrophenyl)imidazo[4,5-f][1,10]phenanthroline (NPIP) ligands, allowed the monitoring of very small changes in the ligands electronic nature. Complexes containing a systematic variation of the position (para, meta, and ortho) of the nitrile terminal group on the ligand (the para being 2-(4-cyanophenyl)imidazo[4,5-f][1,10]phenanthroline (p-CPIP), the meta 2-(3-cyanophenyl)imidazo[4,5-f][1,10]phenanthroline (m-CPIP) and 2-(2-cyanophenyl)imidazo[4,5-f][1,10]phenanthroline (o-CPIP)) were also characterised. Absorption, emission characteristics, and luminescence yields were calculated and correlated with structural variation. It was found that both the electronic changes in the aforementioned ligands showed very small spectral changes with an accompanying complex relationship when examined with traditional electronic methods. Stokes shift and Raman spectroscopy were then employed as a means to directly gauge the effect of polypyridyl ligand change on the conjugation and vibrational characteristics of the complexes. Vibrational coherence as measured as a function of the shifted frequency of the imizodale bridge was shown to accurately describe the electronic coherence and hence vibrational cooperation from the ruthenium centre to the main polypyridyl ligand. The well-defined trends established and elucidated though Raman spectroscopy show that the variation of the polypyridyl ligand can be monitored and tailored. This allows for a greater understanding of the electronic and excited state characteristics of the ruthenium systems when traditional electronic spectroscopy lacks the sensitivity.

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35

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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36

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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37

Kubík, Richard, Stanislav Böhm, Vladimír Havlíček, and Josef Kuthan. "Photoisomerization of imidazo[l,2-a]pyridines." Mendeleev Communications 6, no. 6 (January 1996): 225–26. http://dx.doi.org/10.1070/mc1996v006n06abeh000734.

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38

Böhm, Stanislav, Richard Kubík, Martin Hradilek, Jan Němeček, Michal Hušák, Svetlana Pakhomova, Jan Ondráček, Bohumil Kratochvíl, and Josef Kuthan. "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 by the transformation of the base I into salts III - VII.

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39

Yutilov, Yu M., and L. I. Shcherbina. "Preparation of 2-aryl-substituted imidazo[4,5-b]pyridines and imidazo[4,5-c]pyridines." Chemistry of Heterocyclic Compounds 23, no. 5 (May 1987): 529–35. http://dx.doi.org/10.1007/bf00476381.

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40

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

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

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41

Aginagalde, Maialen, Yosu Vara, Ana Arrieta, Ronen Zangi, Vicente L. Cebolla, Arantzazu Delgado-Camon, and Fernando P. Cossio. "ChemInform Abstract: Tandem [8 + 2] Cycloaddition-[2 + 6 + 2] Dehydrogenation Reactions Involving Imidazo[1,2-a]pyridines and Imidazo[1,2-a]pyrimidines." ChemInform 41, no. 36 (August 12, 2010): no. http://dx.doi.org/10.1002/chin.201036124.

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42

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

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Syntheses are reported for some 3-( benzamido-and fluorobenzamido -methyl)-6-( fluoro , chloro and methylthio )-2(4-methyl-, 4-t-butyl-, 4-cyclohexyl- and 3,4-methylenedioxy-phenyl) imidazo-[1,2-b] pyridazines from the relevant 3-unsubstituted imidazo [1,2-b] pyridazines and the N-( hydroxymethyl ) benzamides. In tests of the ability of these compounds to displace [3H]diazepam from rat brain membrane, 3-(3- or 4-fluorobenzamidomethyl)-2-(3,4-methylenedioxyphenyl)-6-methylthioimidazo[1,2-b]- pyridazine bound most strongly, with IC50 2nM; but in behavioural tests in rats the most active compounds were 6-chloro(and methylthio )-3-(2-fluorobenzamidomethyl)-2-(3,4-methylenedioxyphenyl) imidazo [1,2-b] pyridazines which showed a significant anxiolytic activity at 2.5 mg/kg.

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43

Hung, Tran, Nguyen Quan, Hoang Van Dong, Trinh Nguyen, Hoang Anh, Trieu Hung, Nguyen Van Tuyen, Ngo Thuan, Tuan Dang, and Peter Langer. "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 (January 10, 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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44

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

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

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45

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 major imidazo[1,2-a]pyridines 7a-7c and minor pyrroles 8a-8c. Some mechanistic aspects of the oxidation procedure are discussed in connection with a resistance of 2,6-diphenyl-1,3,5-trimethylpyridinium perchlorate (9c) towards the oxidizing agents.

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46

Barlin, GB, LP Davies, and MML Ngu. "Imidazo[1,2-b]Pyridazines. VIII. Syntheses and Central Nervous System Activities of Some 6-Benzylamino (and methoxybenzylamino)-3-methoxy-2-phenyl(Substituted phenyl or pyridinyl)imidazo[1,2-b]pyridazines." Australian Journal of Chemistry 42, no. 10 (1989): 1759. http://dx.doi.org/10.1071/ch9891759.

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Syntheses and IC50 values for the displacement of 3H-diazepam from rat brain plasma membrane are reported for a series of 6-benzylamino(and methoxybenzylamino )-3-methoxy-2-phenyl(substituted phenyl and pyridinyl )imidazo[l,2-b]pyridazines (and their 6-anilino and 6-phenethylamino analogues). The results are compared with those reported previously (by us) for the 6-chloro, 6-phenoxy, 6-benzylthio, and 6-benzyloxy compounds. In the imidazo[l,2-b]pyridazine ring system, 6-(o- and m- methoxybenzylamino ) groups were found to be beneficial to binding activity; eight compounds have been prepared with IC50 values less than 2 nM (cf. 3H-diazepam with IC50 of 4.2 nM ).2-(p-Aminopheny1)-3-methoxy- 6-(m- methoxybenzylamino )imidazo[1,2-b]pyridazine exhibited the highest activity with IC50 1.0 nM.

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47

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 (September 1, 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. Also, 2 reacted with DMF-DMA to yield the formamidine 15, which in turn, reacted with active methylene reagents, yielding the corresponding pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines 18 and 23a-23d.Key words: 1H-pyrazolo[3,4-b]pyridines, imidazo[1',2':1,5]pyrazolo[3,4-b]pyridines, pyrido[2',3':3,4]pyrazolo[1,5-a]pyrimidines.

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48

Lei, Ying Jie, De Qiang Li, Jie Ouyang, and Ji Xian Shi. "Synthesis and Optical Properties of 2-(1H-Imidazo [4,5-] Phenazin-2-yl) Phenol Derivatives." Advanced Materials Research 311-313 (August 2011): 1286–89. http://dx.doi.org/10.4028/www.scientific.net/amr.311-313.1286.

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A convenient one-pot process to synthesize 2-(1H-imidazo[4,5-b]phenazin-2-yl) phenol derivatives 3a-e with substitute (s) X (X = H, CH3O, CH2OH, Cl, Br) via the reaction of 2-hydroxy aromatic aldehydes with phenazine-2,3-diamines in the presence of manganese(III) acetate at room temperature in 80-85% yield was developed. Meanwhile, the ultraviolet absorption and the fluorescent spectra of these o-hydroxy derivatives of 1H-imidazo[4,5-b] phenazin were measured in methanol. Compared with the dual emission characteristics of 2-(2-hydroxy-phenyl) benzimidazole derivatives, only one fluorescence band with a peak wavelength of 540nm was observed and that the Stokes shifts were around 136-140 nm for 3a-e.

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49

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 (November 18, 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 imidazo[1,2-a]pyrazine-2-carboxylate (4), which on hydrolysis with NaOH yields imidazo[1,2-a]pyrazine-2-carboxylic acid (5). The structures of the newly synthesized compounds have been elucidated on the basis of spectral (IR, 1H and 13C NMR and MS) and analytical data. Compounds 7a-l have also been screened for their antimicrobial activity. Some of the compounds exhibit promising antimicrobial activity

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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 was found that 3-сhloro-4-[(3,4-dihydro-2H-benzo[4,5]imidazo[2,1-b][1,3]thiazin-3-yl)oxy]benzonitrile 4k and 4-сhloro-3-[(6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazin-6-yl)oxy]benzonitrile 4e have the most stable inhibitory effect; and 6-(2,4-dinitrophenoxy)-6,7-dihydro-5H-imidazo[2,1-b][1,3]thiazine 4c and 3-(2,4-dinitrophenoxy)-3,4-dihydro-2H-benzo[4,5]imidazo[2,1-b][1,3]thiazine 4j show the best growth stimulating activity at the concentration of 0.0001%.

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