- Convenient multi-gram scale synthesis of polybrominated imidazoles building blocks
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The multi-gram scale polybromination of variously substituted imidazoles has been realized using a stoichiometric amount of the Br2-DMF complex. Good yields have been obtained compared to other methods using large amounts of acetic acid-sodium acetate buffer.
- Bahnous, Mebarek,Mouats, Chabane,Fort, Yves,Gros, Philippe C.
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Read Online
- Asymmetric synthesis and biological evaluation of imidazole- and oxazole-containing synthetic lipoxin A4 mimetics (sLXms)
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Lipoxins (LXs) are endogenously generated eicosanoids with potent bio-actions consistent with attenuation of inflammation. The costly synthesis and metabolic instability of LXs may limit their therapeutic potential. Here we report the synthesis and charac
- de Gaetano, Monica,Butler, Eibhlín,Gahan, Kevin,Zanetti, Andrea,Marai, Mariam,Chen, Jianmin,Cacace, Antonino,Hams, Emily,Maingot, Catherine,McLoughlin, Alisha,Brennan, Eoin,Leroy, Xavier,Loscher, Christine E.,Fallon, Padraic,Perretti, Mauro,Godson, Catherine,Guiry, Patrick J.
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- Imidazole-Fused Enediynes by Selective C5-C4 Alkynylations of 4,5-Dibromoimidazoles
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An efficient synthesis of symmetrical 1,2-disubstituted 4,5-dialkynylimidazoles by Sonogashira alkynylation of the corresponding 4,5-dibromo derivatives was developed. Moreover, through a careful tuning of the palladium ligand, unsymmetrical 1,2-disusbtituted 4,5-dialkynylimidazoles were also prepared through a regioselective C5 alkynylation of 4,5-dibromoimidazoles, followed by a second alkynylation involving the 4-bromo derivatives so obtained. This interesting class of imidazole-fused enediynes is also able to give thermal Bergman cycloaromatization (BC), as proved by DSC experiments.
- Lessi, Marco,Panattoni, Alessandro,Guglielmero, Luca,Minei, Pierpaolo,Bellina, Fabio
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p. 933 - 943
(2019/02/10)
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- HETEROCYCLIC LIPXON ANALOGS AND USES THEROF
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The present invention relates to a compound of formula (I): wherein L is an optionally substituted heterocyclic group excluding unsubstituted monocyclic pyridine groups; wherein a is 0, 1 or 2; wherein R1 is H or with R2 is a bond; wherein R2 is an optionally substituted alkoxy or aryloxy group, or with R1 forms a bond; wherein R3 is an optionally substituted alkyl group; and wherein R4 is CH2, CMe2 or O. Such compounds may be used in the treatment or prophylaxis of a disease or condition in which inhibition of acute inflammation and/or promotion of its resolution and/or suppression of fibrosis.
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Page/Page column 74
(2018/03/09)
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- Synthesis, crystal structure and antibacterial activity of new highly functionalized ionic compounds based on the imidazole nucleus
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Several new highly functionalized imidazolium derivatives were synthesized, via appropriate synthetic routes, using imidazole, 1-methylimidazole and 2-phenyl-1-methylimidazole as key intermediates. The antibacterial activity of the prepared compounds was evaluated against: Escherichia coli, Staphylococcus aureus, Pseudomonas aeruginosa and Salmonella thipymurium using disk-diffusion and MIC methods. Crystal X-ray structures are reported for six compounds.
- Bahnous, Mebarek,Bouraiou, Abdelmalek,Chelghoum, Meryem,Bouacida, Sofiane,Roisnel, Thierry,Smati, Farida,Bentchouala, Chafia,Gros, Philippe C.,Belfaitah, Ali
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p. 1274 - 1278
(2013/03/14)
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- Development of an efficient process towards the benzimidazole BYK308944: A key intermediate in the synthesis of a potassium-competitive acid blocker
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An entirely new synthesis of the important benzimidazole building block BYK308944 was elaborated using the Stobbe reaction as central element. BYK308944 constitutes an important intermediate for the preparation of 3,6,7,8-tetrahydrochromeno[7,8-d] imidazoles as potassium-competitive acid blockers. The new route relies on the hydroxymethylation of 1,2- dimethylimidazole as cheap starting material followed by oxidation of the corresponding alcohol and Stobbe condensation of the resulting aldehyde with diethyl succinate. All synthetic steps of this new approach were optimized particularly with the goal to establish a process amenable for large- scale preparation.
- Webel, Matthias,Palmer, Andreas Marc,Scheufler, Christian,Haag, Dieter,Mueller, Bernd
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experimental part
p. 142 - 151
(2010/04/29)
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- Reactions of 1,2-Dimethylimidazole, Particularly its Metallation
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A re-examination of the metallation of 1,2-dimethylimidazole has shown that, after quenching of reaction mixtures with suitable reagents, single products may arise from substitution either in the 2-methyl group or in the 5-position or mixtures of both products may arise, depending on the metallating reagent, solvent, and reaction conditions. 1,2-Dimethylimidazol-5-yl-lithium was prepared by reaction of 1,2-dimethyl-5-trimethylstannylimidazole (13) with n-butyl-lithium in tetrahydrofuran at -100 deg C.The corresponding 5-trimethylsilyl compounds (12) was metallated by n-butyl-lithium exclusively in the 2-methyl group. 1,2-Dimethylimidazol-5-yl-lithium was shown to undergo transmetallation reactions at temperatures higher than -100 deg C.An improved procedure is given for the synthesis of 1,2-dimethylimidazole-5-carbaldehyde via hydroxymethylation of 1,2-dimethylimidazole and oxidation of the 5-hydroxymethyl group with nitric acid.
- Iddon, Brian,Lim, Bee Lan
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p. 271 - 277
(2007/10/02)
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