- Synthesis of new highly functionalized 1h-indole-2-carbonitriles via cross-coupling reactions
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An approach for the preparation of polysubstituted indole-2-carbonitriles through a cross-coupling reaction of compounds 1-(but-2-ynyl)-1H-indole-2-carbonitriles and 1-benzyl-3-iodo-1H-indole-2-carbonitriles is described. The reactivity of indole derivatives with iodine at position 3 was studied using cross-coupling reactions. The Sonogashira, Suzuki–Miyaura, Stille and Heck cross-couplings afforded a variety of di-, tri-and tetra-substituted indole-2-carbonitriles.
- Hrizi, Asma,Cailler, Manon,Romdhani-Younes, Moufida,Carcenac, Yvan,Thibonnet, Jér?me
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- Super acid catalysed sequential hydrolysis/cycloisomerization of o-(acetylenic)benzamides under microwave condition: Synthesis, antinociceptive and antiinflammatory activity of substituted isocoumarins
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Synthesis of isocoumarins and related compounds via triflic acid promoted hydrolysis/cyclization sequence of 2-(alkynyl)benzamides under microwave condition was achieved. The substrate scope of the reaction was broad to include not only aromatic but also
- Praveen, Chandrasekaran,Dheenkumar,Perumal
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- Carbopalladation of nitriles: Synthesis of 2,3-diarylindenones and polycyclic aromatic ketones by the Pd-catalyzed annulation of alkynes and bicyclic alkenes by 2-iodoarenenitriles
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2-Iodobenzonitrile, its derivatives, and various heterocyclic analogues undergo palladium(O)-catalyzed annulation onto diarylacetylenes or bicyclic alkenes to afford 2,3-diarylindenones and polycyclic aromatic ketones in very good to excellent yields. This reaction represents one of the first examples of the addition of an organopalladium moiety to the carbon-nitrogen triple bond of a nitrile. The reaction is compatible with a number of functional groups. A reaction mechanism, as well as a model accounting for the electronic effects of substituents on the aromatic ring of the nitrile, is proposed.
- Pletnev, Alexandre A.,Tian, Qingping,Larock, Richard C.
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p. 9276 - 9287
(2007/10/03)
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- Ring Contraction of 2-Azidoquinoline and Quinoxaline 1-Oxides
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Thermal ring contraction of 2-azidoquinoline 1-oxide with loss of nitrogen did not lead to the desired 2-cyano-1-hydroxyindole.Instead, 2-cyanoisatogen (9), 2,2'-dicyano-3,3'-bis (10), and 2-aminoquinoline 1-oxide (7) were formed.The mechanism is believed to involve an intermolecular addition to the intermediate cis-o-nitrosocinnamonitrile formed in a concerted ring-opening nitrogen loss, i.e., not involving a nitrene intermediate.In accord with this, both 2-azido-4-methylquinoline 1-oxide and 2-azidoquinoxaline 1-oxide give the expected 2-cyano-1-hydroxy-3-methylindole (18) and 2-cyano-1-hydroxybenzimidazole (26), respectively.
- Abramovitch, Rudolph A.,Cue, Berkeley W.
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p. 5316 - 5319
(2007/10/02)
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