71683-04-0Relevant academic research and scientific papers
Mechanochemical electrophilic fluorination of liquid beta-ketoesters
Howard, Joseph L.,Sagatov, Yerbol,Browne, Duncan L.
, p. 3118 - 3123 (2017/12/26)
An improved substrate scope for the mechanochemical electrophilic fluorination of dicarbonyls is reported. The applicable substrates have now been broadened to include liquid β-ketoesters. Key to this capability is the inclusion of a grinding auxiliary (NaCl) to improve mass transfer and prevent pasting or gumming of the reaction mixture. Notably, the use of a small amount of acetonitrile is critical to increasing the rate of reaction, ensuring complete consumption of starting materials during the short reaction times as well as improving the selectivity for the monofluorinated product in the mill.
New synthesis of fluorinated pyrazoles
Surmont, Riccardo,Verniest, Guido,De Kimpe, Norbert
supporting information; experimental part, p. 4648 - 4651 (2010/12/19)
A new synthesis of fluorinated pyrazoles, a class of compounds with potential in medicinal chemistry, is described. The treatment of benzoylfluoroacetonitrile with hydrazine yielded the expected new 3-amino-4-fluoropyrazole, while the analogous reaction of α-cyano-α, α-difluoroketones with hydrazine in refluxing isopropanol surprisingly gave rise to 3-unsubstituted 4-fluoropyrazoles via an unprecedented mechanism. The isolation of intermediate hydrazine adducts led to a mechanistic rationale for this transformation.
Convenient fluorination of nitro and nitrile compounds with Selectfluor
Peng, Weimin,Shreeve, Jean'ne M.
, p. 4905 - 4909 (2007/10/03)
A variety of nitro and nitrile compounds were fluorinated in good yields by Selectfluor under mild conditions. For these transformations to be successful, it is crucial to select proper amounts of an appropriate base as a function of the properties of the substrate and also to use Selectfluor only as required.
Potential antiarthritic agents. II. Benzoylacetonitriles and β-aminocinnamonitriles
Ridge,Hanifin,Harten,Johnson,Menschik,Nicolau,Sloboda,Watts
, p. 1385 - 1389 (2007/10/09)
Benzoylacetonitrile and β-aminocinnamonitrile are shown to possess potent intiinflammatory activity in the rat adjuvant arthritis model. In a series of phenyl-substituted analogues, only o-, m-, and p-fluorobenzoylacetonitrile and m- and p-fluoro-β-aminocinnamonitrile retained activity. Additionally, β-amino-2- and β-amino-3-thiopheneacrylonitrile and β-oxo-2- and β-oxo-3-thiophenepropionitrile exhibited similar activity. These agents are not believed to be acting via prostaglandin synthetase inhibition. The metabolic profile of benzoylacetonitrile is also described.
