7346-22-7Relevant academic research and scientific papers
Propyl–SO3H functionalized SBA-15: Microwave-mediated green synthesis of biologically active multi-substituted imidazole scaffolds
Gabla, Jenifer J.,Lathiya, Dharmesh R.,Revawala, Akash A.,Maheria, Kalpana C.
, p. 1863 - 1881 (2019/01/04)
Abstract: Propylsulfonic acid functionalized Santa Barbara Amorphous-15 (SBA-15–Pr–SO3H) catalyst has been synthesized using a surface modification of mesoporous SBA-15 via the one-pot co-condensation method. The synthesized SBA-15–Pr–SO3H has been characterized by peculiar characterization techniques such as small- and wide-angle XRD, SEM–EDX, TEM, TG–DTA, acidity, FT-IR, Py-FT-IR and BET surface area analysis. The catalytic activity of synthesized catalyst has been studied towards solvent-free MW irradiation for the green and rapid synthesis of multi-substituted imidazoles, [2,4,5-triphenyl-1(H)-imidazole (tri-imidazole) and 1-benzyl-2,4,5-triphenyl-1H-imidazole (tetra-imidazole)]. The SBA-15–Pr–SO3H catalyst was found to be an efficient and recyclable solid acid catalyst and this solvent-free MW protocol afforded products in good to excellent yields of both, tri and tetra imidazoles (> 95%) within shorter reaction time (3?min) at 600?W as compared to the SBA-15 and other existing protocols. The applicability of this protocol was further explored by conducting the experiments in the presence of varied solvents and substituted aldehydes to generate a library of both, tri- and tetra-imidazole scaffolds. The catalyst was found to be reusable up to several runs without loss of its catalytic activity. This report allows the rapid and scalable access to a variety of multi-substituted imidazoles using SBA-15–Pr–SO3H, as heterogeneous catalyst. Graphical abstract: SBA-15–Pr–SO3H catalyzed solvent-free MW assisted green synthesis of multi-substituted imidazoles via MCRs.[Figure not available: see fulltext.].
Non–symmetrically p–nitrobenzyl–substituted N–heterocyclic carbene–silver(I) complexes as metallopharmaceutical agents
Shahini,Achar, Gautam,Budagumpi, Srinivasa,Tacke, Matthias,Patil, Siddappa A.
, (2017/09/30)
In the present work, a series of eight new imidazole, 4,5–dichloroimidazole, 4,5–diphenylimidazole and benzimidazole based nitro–functionalized mono–N–heterocyclic carbene (NHC)–silver(I) acetate (7a–d) and bis–NHC–silver(I) hexafluorophosphate complexes (8a–d) were synthesised by the reaction of the corresponding azolium hexafluorophosphate salts (6a–d) with silver(I) acetate and silver(I) oxide in methanol and acetonitrile, respectively. All the synthesised compounds were fully characterized by various spectroscopic techniques and elemental analyses. Additionally, the structure of bis–(1–benzyl–3–(p–nitrobenzyl)–4,5–dichloroimidazole–2–ylidene)silver(I) hexafluorophosphate complex (8b) was confirmed by single crystal X–ray diffraction analysis. Preliminary in vitro antibacterial evaluation was conducted for all the compounds (6a–d), (7a–d), and (8a–d) by Kirby–Bauer's disc diffusion method followed by the determination of Minimum Inhibitory Concentration (MIC) from broth macrodilution method against five standard bacteria; two Gram–positive bacterial strains (Staphylococcus aureus and Bacillus subtilis) and three Gram–negative bacterial strains (Escherichia coli, Shigella sonnei, and Salmonella typhi). All the hexafluorophosphate salts (6a–d) were found inactive against the tested bacterial strains and their corresponding mono– and bis–NHC–silver(I) complexes (7a–d and 8a–d) exhibited moderate to high antibacterial activity with MIC value in the range 8–128?μg/mL. In addition, preliminary in vitro anticancer potential of all the silver(I) complexes (7a–d and 8a–d) was determined against the human derived breast adenocarcinoma cells (MCF 7) by MTT assay. All the mono– and bis–NHC–silver(I) complexes (7a–d and 8a–d) orchestrated high anticancer potential with IC50 values ranging from 10.39 to 59.56?nM. In comparison, mono– NHC–silver(I) complexes performed better than the bis–NHC–silver(I) complexes.
Isonitrile alkylations: A rapid route to imidazo[1,5-a]pyridines
Li, Yajun,Chao, Allen,Fleming, Fraser F.
supporting information, p. 2111 - 2113 (2016/02/05)
Metalated arylmethylisonitriles readily add to 2-chloropyridines to afford imidazo[1,5-a]pyridines. Analogous additions to imidoyl chlorides and a chloroquinoline provide imidazoles and an imidazo[1,5-a]quinolone which, like imidazo[1,5-a]pyridines, are v
An efficient and one-pot synthesis of 2,4,5-trisubstituted and 1,2,4,5-tetrasubstituted imidazoles catalyzed by InCl3·3H2O
Das Sharma, Saikat,Hazarika, Parasa,Konwar, Dilip
, p. 2216 - 2220 (2008/09/18)
InCl3·3H2O was found to be a mild and effective catalyst for the efficient, one-pot, three component synthesis of 2,4,5-trisubstituted imidazoles at room temperature. Moreover, the utility of this protocol was further explored conveniently for the one-pot, four component synthesis of 1,2,4,5-tetrasubstituted imidazoles in high yields.
Reactions of 2-unsubstituted 1H-imidazole 3-oxides with 2,2-bis(trifluoromethyl)ethene-1,1-dicarbonitrile: A stepwise 1,3-dipolar cycloaddition
Mloston, Grzegorz,Jasinski, Marcin,Linden, Anthony,Heimgartner, Heinz
, p. 1304 - 1316 (2007/10/03)
The reaction of 1,4,5-trisubstituted 1H-imidazole-3-oxides 1 with 2,2-bis(trifluoromethyl)ethene-1,1-dicarbonitrile (7, BTF) yielded the corresponding 1,3-dihydro-2H-imidazol-2-ones 10 and 2-(1,3-dihydro-2H-imidazol- 2-vlidene)malononitriles 11, respectiv
Synthesis and analgesic activity of some 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole derivatives
Ucucu, Uemit,Karaburun, Nalan Guendogdu,Isikdag, Ilhan
, p. 285 - 290 (2007/10/03)
In this study, derivatives of 1-benzyl-2-substituted-4,5-diphenyl-1H-imidazole were synthesized and their analgesic activity assayed in two tests. 1,2,4,5-Tetrasubstituted imidazole compounds were obtained by the treatment of purified imidazole compounds with benzyl chloride in the presence of sodium hydride. The structure elucidation of the compounds was performed by IR, 1H-NMR and mass spectroscopic data and elemental analysis results. Generally the prepared compound exhibited only moderate analgesic activity in mice at the dose of 100 mg/kg i.p.; however, a few of them exhibited good activity, almost equivalent to that of morphine at 1 mg/kg i.p. was observed. At the above dosage, no toxicity was observed for all compounds. Copyright
5,10,15,20-Tetrakis(N-protected-imidazol-2-yl)porphyrins
Milgrom, Lionel R.,Dempsey, Philip J.F.,Yahioglu, Gokhan
, p. 9877 - 9890 (2007/10/03)
It is shown that examples of title porphyrins can be prepared from suitably N-protected imidazole-2-carboxaldehydes and pyrrole in refluxing propionic acid: subsequent deprotection, affords a synthetic route to 5,10,15,20-tetrakis(substituted-imadizol-2-y) porphyrins (TIPs).
