• Citer

An unexpected ring-opening in the reissert reaction on 2,3-diphenylquinoxaline-n-oxide.

par Nasielski, Jacques ;Heilporn, Sylvie ;Hinkens, Raymonde ;Tinant, Bernard;Declercq, J.P.
Référence Tetrahedron, 45, 24, page (7795-7804)
Publication Publié, 1989

Article révisé par les pairs

• Détails
• Contenu

Résumé :

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 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. © 1989.