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Paper | Regular issue | Vol 29, No. 7, 1989, pp.1325-1329
Published online, 1st January, 1970
DOI: 10.3987/COM-89-4980
Nucleophilic Aromatic substitution in 4,5-Dicyanoimidazoles

Paul G. Apen and Paul G. Rasmussen*

*Department of Chemisry, University of Michigan , 930 North University, Ann Arbor, MI 48109-1055, U.S.A.

Abstract

Nucleophilic aromatic substitution reactions in 4,5-dicyanoimidazoles are described. For example, reaction of 1-methyl-2-bromo-4,5-dicyanoimidazole (5) with good nitrogen nucleophiles, such as n-butylamine, piperidine and imidazole, gave the highly functionalized 2-substituted 1-methyl-4,5-dicyanoimidazoles (6-10). Reaction of 5 with weaker nucleophiles, such as carbazole, did not occur.