- Facile synthetic method for diverse polyfunctionalized imidazoles by means of pd-catalyzed C-H bond arylation of N -methyl-4,5-dibromoimidazole
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C-H bond-selective arylation reaction of 4,5-dibromoimidazole with aryl iodides, catalyzed by the palladium-1,10-phenanthroline complex [Pd(phen) 2](PF6)2, has been developed. The process tolerates the presence of a variety of functional groups on the aryl halide substrates. The products formed in these reactions were transformed to a variety of polyfunctionalized imidazoles by taking advantage of selective reactions of remaining C-Br bonds.
- Yamauchi, Takayuki,Shibahara, Fumitoshi,Murai, Toshiaki
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p. 7185 - 7192
(2014/08/18)
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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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- Aminobenzoannulated hetero- and carbocycles from 2-azahepta-2,4-dien-6- ynyllithium compounds: Scope and limitation of a novel benzoannulation reaction
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Deprotonation of the N-benzylhetarylmethanimines 9, 12, 15, and 18 at -78°C with subsequent warming to room temperature over 16 hours and treatment with electrophiles furnished polysubstituted aminobenzoannulated heterocycles 19-25 in good to excellent yields. In a similar fashion, the deprotonation of the N-allyl-2-(alk-1-ynyl)phenylmethanimines 26 and 27 led to 2-vinylnaphthalen-1-amines 28 and 29, respectively, in moderate yields. The reaction of N-[(trimethylsilyl)methyl]imine 31 afforded naphthalen-1-amine 33, unsubstituted at the ortho position after removal of the trimethylsilyl group. The deprotonation of imine 34, bearing a trimethylsilyl group on the C≡C bond, gave none of expected amines, but the substituted imine 35, whose structure was identified using 2D NMR spectroscopy. Georg Thieme Verlag Stuttgart.
- Lyaskovskyy, Volodymyr,Froehlich, Roland,Wuerthwein, Ernst-Ulrich
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p. 2135 - 2144
(2008/03/28)
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- 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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p. 1949 - 1951
(2007/10/03)
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