Selective Synthesis of 2-, 4-, and 5-Cyano Substituted Imidazoles from Imidazole N-Oxides and Trimethylsilyl Cyanide.
1-Substituted 2-, 4-, and 5-cyanoimidazoles were produced by reaction of 3-cyclohexyl or 3-p-tolylimidazole 1-oxide and trimethylsilyl cyanide in the presence of triethylamine. The product composition depended on reaction temperature and solvent polarity. By proper choice of these parameters each isomer could be obtained selectively in reasonable yield.
Alcázar
Jesús
J
Facultad de Química, Universidad de Castilla-La Mancha, E-13071 Ciudad Real, Spain, and Department of Medicinal Chemistry, Royal Danish School of Pharmacy, DK-2100 Copenhagen, Denmark.
Begtrup
Mikael
M
de La Hoz
Antonio
A