78950-32-0Relevant articles and documents
Synthesis of primary amides by aminocarbonylation of aryl/hetero halides using non-gaseous NH3 and CO sources
Suresh,Baburajan, Poongavanam,Ahmed, Mansur
supporting information, p. 4864 - 4867 (2015/07/28)
Abstract A practically simple method for the synthesis of primary amides via the palladium-catalysed aminocarbonylation of aromatic halides by using solid sources of gaseous ammonia and carbon monoxide is described. The system tolerated a wide variety of hindered and functionalized aryl/hetero halides and afforded good to excellent yields (69-94%) of the amide. Pharmacologically active Exalamide and Pyrazinecarboxamide were synthesised in high yields to demonstrate the effectiveness of this method.
Gold Activation of Nitriles: Catalytic Hydration to Amides
Ramon, Ruben S.,Marion, Nicolas,Nolan, Steven P.
supporting information; experimental part, p. 8695 - 8697 (2010/03/24)
A gold-based catalytic system that efficiently mediates the hydration of a broad spectrum of nitriles, including aromatic, heteroaromatic and aliphatic examples and efficiently catalyze the hydration of a range of organonitriles has been reported. Nitriles are considered inert in the context gold catalysis and have only been used as reaction solvent or as throw-away ligands in well-defined cationic gold catalysis. The obtained product was purified by flash chromatography using a gradient of pentane/ethyl acetate and compound 1 was isolated as a colorless solid. Aromatic substrates bearing two nitrile groups as in rn-benzenedinitrile and p-benzenedinitrile underwent double nitrile hydration and afforded excellent yields in the corresponding diamides. There is high relevance for the use of cationic gold complexes bearing such ligands and should have important implications in catalysis.
Synthesis of 3-substituted benzamides and 5-substituted isoquinolin-1(2H)-ones and preliminary evaluation as inhibitors of poly(ADP-ribose)polymerase (PARP)
Watson, Corrine Y.,Whish, William J. D.,Threadgill, Michael D.
, p. 721 - 734 (2007/10/03)
Inhibitors of poly(ADP-ribose)polymerase (PARP) inhibit repair of damaged DNA and thus potentiate radiotherapy and chemotherapy of cancer. 3-Substituted benzamides and 5-substituted isoquinolin-1-ones have been synthesised and evaluated for inhibition of PARP. Reduction of 3-(bromoacetyl)benzamide, followed by treatment with base, gave RS-3-oxiranylbenzamide. Reduction of 3-(hydroxyacetyl)benzonitrile with bakers' yeast gave the R-diol which was converted to R-3-(1,2-dihydroxyethyl)benzamide. Similar reduction of 3-(acetoxyacetyl)benzonitrile led towards the S-diol which was converted to its cyclic acetonide. E-2-(2,6-Dicyanophenyl)-N,N-dimethylethenamine was formed by condensation of 2,6-dicyanotoluene with dimethylformamide dimethyl acetal (DMFDMA); cyclisation under acidic conditions afforded 5-cyanoisoquinolin-1-one. Heck coupling of 5-iodoisoquinolin-1-one with propenoic acid formed E-3-(1-oxoisoquinolin-5-yl)propenoic acid. 3-Oxiranylbenzamide, 5-bromoisoquinolin-1-one and 5-iodoisoquinolin-1-one were among the most potent inhibitors of PARP activity in a preliminary screen in vitro. Copyright (C) 1998 Elsevier Science Ltd.
