87544-83-0Relevant academic research and scientific papers
C?H Cyanation of 6-Ring N-Containing Heteroaromatics
Elbert, Bryony L.,Farley, Alistair J. M.,Gorman, Timothy W.,Johnson, Tarn C.,Genicot, Christophe,Lallemand, Bénédicte,Pasau, Patrick,Flasz, Jakub,Castro, José L.,MacCoss, Malcolm,Paton, Robert S.,Schofield, Christopher J.,Smith, Martin D.,Willis, Michael C.,Dixon, Darren J.
, p. 14733 - 14737 (2017)
Heteroaromatic nitriles are important compounds in drug discovery, both for their prevalence in the clinic and due to the diverse range of transformations they can undergo. As such, efficient and reliable methods to access them have the potential for far-reaching impact across synthetic chemistry and the biomedical sciences. Herein, we report an approach to heteroaromatic C?H cyanation through triflic anhydride activation, nucleophilic addition of cyanide, followed by elimination of trifluoromethanesulfinate to regenerate the cyanated heteroaromatic ring. This one-pot protocol is simple to perform, is applicable to a broad range of decorated 6-ring N-containing heterocycles, and has been shown to be suitable for late-stage functionalization of complex drug-like architectures.
1-ACYLOXYPYRIDINIUM ION: THE REACTIVE INTERMEDIATE IN A MODIFIED REISSERT-HENZE REACTION
Fife, Wilmer K.,Boyer, Brett D.
, p. 1121 - 1124 (2007/10/02)
Cyanation of 3-X-1-dimethylaminocarbonyloxypyridinium ions with trimethylsilanecarbonitrile or cyanide ion gives 3-methyl-2-pyridinecarbonitrile (ca.90percent) contaminated with 5-methyl-2-pyridinecarbonitrile (ca.10percent) when X = -CH3, and approximately equal amounts of the 3- and 5-X derivatives when X = -COOCH3.These product mixtures are identical to those obtained with the corresponding pyridine 1-oxides and dimethylcarbamoyl chloride in a modified Reissert-Henze reaction.
