3-Acetyl-2-amino-4-hydroxy-1,3-pentadienecarbonitrile:E,Z-isomerism and the ability to form chelates

The Ni acetylacetonate-catalyzed addition of acetylacetone to malononitrile was shown to afford 3-acetyl-2-amino-4-hydroxy-1,3-pentadienecarbonitrile. The diphenyl boron chelate of the latter with a -diketone-type structure was obtained.E,Z-isomerism of the chelate and the free ligand were investigated. TheZ-isomers were found to dominate in low polarity solvents.The work was supported by the Russian Foundation for Basic Research (Project No. 94-03-08964).Translated fromIzvestiya Akademii Nauk. Seriya Khimicheskaya, No. 8, pp. 1432–1435, August, 1994.