NEW PYRIDINECARBONITRILES FROM FLUOROARYLPROPENONES

The facile synthetic approaches to 3-pyridinecarbonitriles are describ ed. The first approach involves the base-catalyzed transformation of 4 -hydroxy-1,1-cyclohexanedicarbonitrile 2a into 4a, b. The other route involves the base-catalyzed multi-step one-pot reaction of aryl methyl ketones with the appropriate arylidenemalononitriles 6, 11a, b. Caref ul study of the synthesis of 2a, b from 1a, b revealed the importance of controlling the reaction conditions. Thus, 1,7-dioxo-4,4-heptanedic arbonitriles 3a, b or 3-pyridinecarbonitrile 4a were obtained in addit ion to the desired 2a, b under different basic conditions.