128620-48-4Relevant articles and documents
AN UNEXPECTED RING-OPENING IN THE REISSERT REACTION ON 2,3-DIPHENYLQUINOXALINE-N-OXIDE.
Nasielski, J.,Heilporn, S.,Nasielski-Hinkens, R.,Tinant, B.,Declercq, J. P.
, p. 7795 - 7804 (2007/10/02)
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+/-6percent) and small amounts of 2-cyanoquinoxaline.Using three equivalents of trimethylsilyl cyanide instead of KCN, and dichloromethane as the solvent, leads to a 72percent yield of 2-cyanoquinoxaline.The reaction of trimethylsilyl cyanide and benzoyl chloride with 2,3-diphenylquinoxaline-N-oxide 2 leads to an unexpected ring-opening product 13; its structure is based on spectroscopic data and on an X-ray crystallographic analysis.
