Y. Ahmad, M. S. Habib, Ziauddin
Oct 1, 1965
Citations
0
Influential Citations
6
Citations
Journal
Bulletin of the Chemical Society of Japan
Abstract
3-Hydroxy-2-phenylquinoxaline 1-oxide (Ia), on being heated with acetyl chloride, instead of giving the acetyl derivative, gives a chloro compound (IIg), with a simultaneous loss of its N-oxide function. Ia, on being refluxed with a mixture of concentrated hydrochloric acid and acetic acid, undergoes the same transformation. Other derivatives (Ib–f) of Ia behave similarly and give the corresponding chlorine-substituted bases (IIh—1), the structure of which has been established by authentic syntheses. A nucleophilic mechanism of this chlorination has been proposed, in which the presence of an oxygen function a position 3 of the 2-substituted quinoxaline 1-oxides seems to direct the chlorine substitution to position 6.