Halogen exchanse between l.methyl.2-bwmo-4,5-dicyanoin,~_,_ole and lithium Β’Idoride in 5.ch'cyanoirddawle, while additional l~atin& to 2100C resulted in the subsequent demetbylation to yie/d 2-chioro-4,5-dicyanoimidawie. The ucleopMiic aromatic 511bstitution reactions of vario~ imidazole ducleophiles with l-m~thyl-2-fluoro-4,5-dicymmimi~le resulted in ~,veral derivatives of 2-(4',5'.dicyano-l'-imidazoyl)-4,5-dicyanoim~oie. The pea, [IV, and electronic properties are reporte~L 0 1999 Elsevier Science Ltd. All fights reserved.
lmtrod~tlom Although examples of C-N connectivity between imidazole rings are relatively rate, there are a few of such 1,2'-dimers reported. Syntheses which link imidazole and benzimidazole ring systems this way have been carried out using NAS reactions on 2,4,5-trichloroimidazole, 1 2-chlorobenzimidazoles, 2 and 1-methyl-2methylsulphonyl-5-nitro imidazole.3 Some of ~ dimer systems have been examined specifically for their pharmaceutical applications? For dicyanoimidazoles, one approach to synthesizing 2-substituted compounds has been through the use of the 2-diazo intermediates. 5