When quinoxaline-N-oxide 1 is reacted with KCN and benzoyl chloride in water (the Reissert reaction) or methanol, the products are 2-, 5-and 6-chloroquinoxaline (the latter being the major product: 42±6%) and small amounts of 2-cyanoquinoxaline. Using three equivalents of trimethylsilyl cyanide instead of KCN, and dichloromethane as the solvent, leads to a 72% yield of 2-cyanoquinoxaline. The reaction of trimethylsilyl cyanide and ...
