Tetrahedron

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

J Nasielski, S Heilporn, R Nasielski-Hinkens, B Tinant…

Index: Nasielski, J.; Heilporn, S.; Nasielski-Hinkens, R.; Tinant, B.; Declercq, J. P. Tetrahedron, 1989 , vol. 45, # 24 p. 7795 - 7804

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Citation Number: 6

Abstract

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 ...