58537-99-8Relevant academic research and scientific papers
Metal-Free Regioselective Monocyanation of Hydroxy-, Alkoxy-, and Benzyloxyarenes by Potassium Thiocyanate and Silica Sulfuric Acid as a Cyanating Agent
Sardarian, Ali Reza,Dindarloo Inaloo, Iman,Modarresi-Alam, Ali Reza,Kleinpeter, Erich,Schilde, Uwe
, p. 1748 - 1756 (2019/02/05)
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.
New Acyloxymethyl Ketones: Useful Probes for Cysteine Protease Profiling
Coman, Anca G.,Paraschivescu, Codruta C.,Hadade, Niculina D.,Juncu, Andrei,Vlaicu, Ovidiu,Popescu, Costin-Ioan,Matache, Mihaela
, p. 3917 - 3923 (2016/11/11)
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.
A general methodology for the synthesis of substituted phenols from pyranone precursors
Marshall, Laura J.,Cable, Karl M.,Botting, Nigel P.
scheme or table, p. 457 - 459 (2011/04/24)
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
The synthesis of substituted phenols from pyranone precursors
Marshall, Laura J.,Cable, Karl M.,Botting, Nigel P.
experimental part, p. 8165 - 8170 (2009/12/26)
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.
The Room-Temperature Palladium-Catalyzed Cyanation of Aryl Bromides and Iodides with Tri-t-butylphosphine as Ligand
Ramnauth, Jailall,Bhardwaj, Namrta,Renton, Paul,Rakhit, Suman,Maddaford, Shawn P.
, p. 2237 - 2239 (2007/10/03)
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.
Reductive Desilanolation as a Route to Benzonitriles. An Application to a Concise Synthesis of the Aromatic Sector of Calicheamicin.
Olson, Steven H.,Danishefsky, Samuel J.
, p. 7901 - 7904 (2007/10/02)
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.
