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The one-pot reaction of aromatic aldehydes, malononitrile dimer, and triethylamine unexpectedly led to ammonium salts of not previously assumed 5,7-diamino-4-aryl-2-(dicyanomethyl)-1,4-dihydro-1,8-naphthyridine-3,6-dicarbonitriles, but the isomeric 5,7-diamino-4-aryl-2-(dicyanomethyl)-1,4-dihydro-1,6-naphthyridine-3,8-dicarbonitriles. Following neutralization and dehydrogenation led to the new, annulated with pyridine ring tricyanopyridines (TCPy). [ABSTRACT FROM AUTHOR]

The synthesis of nicotinamide derivatives containing a buta-1,3-diene-1,1,3-tricarbonitrile fragment through the base-promoted three-component reaction of an aromatic aldehyde, an acetoacetamide and malononitrile dimer in the presence of an oxidant is reported. The HOMO-LUMO energy levels were estimated by cyclic voltammetry and UV-Vis measurements. The influence of aryl and carbomoyl substituents on the optical and electrochemical properties was also investigated. [ABSTRACT FROM AUTHOR]