- Metal-Free Regioselective Monocyanation of Hydroxy-, Alkoxy-, and Benzyloxyarenes by Potassium Thiocyanate and Silica Sulfuric Acid as a Cyanating Agent
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A novel and efficient metal- and solvent-free regioselective para-C-H cyanation of hydroxy-, alkoxy-, and benzyloxyarene derivatives has been introduced, using nontoxic potassium thiocyanate as a cyanating reagent in the presence of silica sulfuric acid (SSA). The desired products are obtained in good to high yields without any toxic byproducts.
- Sardarian, Ali Reza,Dindarloo Inaloo, Iman,Modarresi-Alam, Ali Reza,Kleinpeter, Erich,Schilde, Uwe
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p. 1748 - 1756
(2019/02/05)
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- New Acyloxymethyl Ketones: Useful Probes for Cysteine Protease Profiling
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Peptidyl-acyloxymethyl ketones (AOMKs) belong to a class of selective, irreversible inhibitors (activity-based probes) widely used as chemical tools of investigating proteins, for example, in activity-based protein profiling. The synthesis of the AOMKs has always been challenging and current methodologies involve both solution and solid-phase synthesis. Herein, the synthesis of a new scaffold useful for the preparation of peptidyl-AOMKs is reported and it is demonstrated that the new synthetic probes bearing a 4-functionalized 2,6-dimethylbenzoate efficiently inhibit cysteine proteases like cathepsin B.
- Coman, Anca G.,Paraschivescu, Codruta C.,Hadade, Niculina D.,Juncu, Andrei,Vlaicu, Ovidiu,Popescu, Costin-Ioan,Matache, Mihaela
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p. 3917 - 3923
(2016/11/11)
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- A general methodology for the synthesis of substituted phenols from pyranone precursors
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Phenols are an important group of organic compounds,1 with many natural products such as polyketides, coumarins and flavonoids containing mono- or poly-phenolic moieties. The synthesis of substituted phenols from pyranone precursors is presented. A variety of pronucleophiles were used in combination with tert-butanol as solvent and potassium tert-butoxide as base, using both conventional heating methods and microwave conditions. Copyright
- Marshall, Laura J.,Cable, Karl M.,Botting, Nigel P.
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scheme or table
p. 457 - 459
(2011/04/24)
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- The synthesis of substituted phenols from pyranone precursors
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The syntheses of various substituted phenols from pyranone precursors, namely 4H-pyran-4-one, 3-(benzyloxy)-2-methyl-4H-pyran-4-one (benzyl-maltol), 2,6-dimethyl-4H-pyran-4-one and diethyl 4-oxo-4H-pyran-2,6-dicarboxylate (diethyl chelidonate) are presented. A variety of pronucleophiles were used in combination with tert-butanol as solvent and potassium tert-butoxide as base, using conventional heating methods and microwave conditions.
- Marshall, Laura J.,Cable, Karl M.,Botting, Nigel P.
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experimental part
p. 8165 - 8170
(2009/12/26)
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- The Room-Temperature Palladium-Catalyzed Cyanation of Aryl Bromides and Iodides with Tri-t-butylphosphine as Ligand
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The palladium-catalyzed cyanation of aryl bromides and iodides to the corresponding nitriles occurs at room temperature when tri-t-butylphosphine is used as ligand, Zn(CN)2 as the cyanide source and Zn dust as a co-catalyst in DMF as solvent. A variety of aromatic halides, including electron-withdrawing and electron-donating, can be efficiently cyanated under these conditions. The reactions are completed in less than 1 hour and products are produced in good to excellent yield.
- Ramnauth, Jailall,Bhardwaj, Namrta,Renton, Paul,Rakhit, Suman,Maddaford, Shawn P.
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p. 2237 - 2239
(2007/10/03)
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- Reductive Desilanolation as a Route to Benzonitriles. An Application to a Concise Synthesis of the Aromatic Sector of Calicheamicin.
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The TMS-cyanohydrins of quinones undergo reductive desilanolation in the presence of samarium iodide to form hydroxybenzonitriles.Benzoquinone 1 was converted to the hexasubstituted aromatic fragment of calicheamicin 4 by this method.
- Olson, Steven H.,Danishefsky, Samuel J.
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p. 7901 - 7904
(2007/10/02)
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