- Preparation of carbazole and dibenzofuran derivatives by selective bromination on aromatic rings or benzylic groups with N-bromosuccinimide
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N-Bromosuccinimide (NBS), a bromine source, has been used to study the bromination of toluidine and cresols systematically to clarify the underlying mechanism and the orientation effect. It has been found that bromination of toluidine and cresols which possess electron-donating NH2/OH with NBS gives electrophilic aromatic substitution products quickly instead of the desired benzylic bromination products. In contrast, when the electronic effect of the substituted groups is reversed, only the benzylic bromination products are gained. Based on this methodology, several potential AChE inhibitors, such as 2-methoxy-5-(benzylamino)methyl-dibenzofuran, 3-bromo-2-methoxy-5-methyl-9H- carbazole, 3,6-dibromo-2-methoxy-5-methyl-9H-carbazole, and 5-(bromomethyl)-2- methoxy-9H-(phenylsulfonyl)-carbazole have been synthesized.
- Fang, Lei,Zhang, Haun,Fang, Xubin,Gou, Shaohua,Cheng, Lin
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p. 635 - 641
(2014/06/23)
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- Effect of structural factors and solvent nature in bromination of anilines
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Reaction of electrophilic bromination of aniline containing various ortho, meta, and para substituents in the aromatic ring was studied. The optimal conditions for synthesis of mono-, di-, tri-, and tetrabromo derivatives of aniline and brominated analog of Aniline Black were found.
- Bagmanov
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experimental part
p. 1570 - 1576
(2011/06/20)
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- Oxidative bromination of aniline and its derivatives
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Oxidative bromination of aniline and its derivatives containing various substituents (CH3, Cl, NO2, COOH) in ortho, meta, and para positions with a brominating mixture of NaBr (KBr) and 20-22% hydrogen peroxide in 6-8% hydrochloric acid at the molar ratio aniline: NaBr (KBr): H 2O2: HCl = 1: 3.5: 3.2: 4.5 is described.
- Salakhov,Bagmanov,Umaeva,Bagmanova
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experimental part
p. 1479 - 1481
(2009/02/05)
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- Efficient Catalysis of Hydrodediazoniations in Dimethylformamide
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For hydrodediazoniations (the replacement of a diazo group by hydrogen) in DMF, several substances act as catalysts through their ability to serve as electron donors and initiate free-radical reactions.A general procedure has been developed in which FeSO4 speeds the conversion and leads to higher yields.Trapping experiments demonstrated the presence of free-radical intermediates.N,N-Dimethylacetamide was found to rival DMF as a source of hydrogen atoms.
- Wassmundt, Frederick W.,Kiesman, William F.
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p. 1713 - 1719
(2007/10/02)
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- Deuteriodediazoniation: A general method for the replacement of a diazonium group by deuterium
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Aromatic amino groups are replaced with deuterium via a diazonium salt intermediate. Dimethylformamide-d7 is the deuterium donor in this mild replacement method that yields aromatic-d1 products in high isotopic purity. The presence of methyl groups lowers the isotopic purity of the products.
- Wassmundt,Kiesman
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p. 281 - 288
(2007/10/02)
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- BROMINATION OF ANILINES BY BENZYLTRIPHENYLPHOSPHONIUM TRIBROMIDE
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Anilines and benzyltriphenylphosphonium tribromide in dichloromethane and methanol medium in the presence of sodium bicarbonate react within a few minutes at room temperature to give the corresponding polybromoanilines in good yields.
- Xin-teng, Ding,Guo-bin, Liu
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p. 1261 - 1266
(2007/10/02)
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- Halogenation Using Quaternary Ammonium Polyhalides. VI. Bromination of Aromatic Amines by Use of Benzyltrimethylammonium Tribromide
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The reaction of aromatic amines with benzyltrimethylammonium tribromide in dichloromethane-methanol containing calcium carbonate powder for 0.5 h at room temperature gave bromo-substituted aromatic amines in good yields.
- Kajigaeshi, Shoji,Kakinami, Takaaki,Inoue, Kazuhisa,Kondo, Manabu,Nakamura, Hiroko,et al.
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p. 597 - 599
(2007/10/02)
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