Synthesis and characterization of derivatives and dimers of 4,5- dicyanoimidazole

Article abstract of DOI:10.1016/S0040-4020(99)00060-5

Synthesis of 1-methyl-2-fluoro-4,5-dicyanoimidazole was accomplished by halogen exchange between 1-methyl-2-bromo-4,5-dicyanoimidazole and potassium fluoride with catalytic 18-crown-6 ether in diglyme. Halogen exchange between 1-methyl-2-bromo-4,5-dicyanoimidazole and lithium chloride in N- methylpyrrolidinone at 150°C yielded 1-methyl-2-chloro-4,5-dicyanoimidazole, while additional heating to 210°C resulted in the subsequent demethylation to yield 2-chloro-4,5-dicyanoimidazole. The nucleophilic aromatic substitution reactions of various imidazole nucleophiles with 1-methyl-2- fluoro-4,5-dicyanoimidazole resulted in several derivatives of 2-(4',5'- dicyano-1'-imidanzoyl)-4,5-dicyanoimidazole. The pKa, UV, and electronic properties are reported.