Tetrahedron p. 7795 - 7804 (1989)
Update date:2022-07-29
Topics:
Nasielski, J.
Heilporn, S.
Nasielski-Hinkens, R.
Tinant, B.
Declercq, J. P.
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.
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Doi:10.1021/ja00177a016
(1990)Doi:10.1039/c5ra01340b
(2015)Doi:10.1021/jo00305a025
(1990)Doi:10.1007/BF00810295
(1990)Doi:10.1021/acs.joc.9b02391
(2019)Doi:10.1021/ja00177a022
(1990)
