Tetrahedron

Deoxygenation of quinoxaline N-oxides and related compounds

MJ Haddadin, GE Zahr, TN Rawdah, NC Chelhot…

Index: Haddadin,M.J. et al. Tetrahedron, 1974 , vol. 30, p. 659 - 666

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Citation Number: 30

Abstract

The alkali induced deoxygenation of 3-(α-hydroxyalkyl)-quinoxaline-1-oxides is shown to be first order in substrate and in hydroxide ion. Examples are given to illustrate the synthetic utility of this reaction for the synthesis of quinoxaline and quinoline derivatives of type 4, 5, 8, and 11. The mechanism of the reaction is related to the mechanism of deoxygenation of heteroaromatic N-oxides by sodium dithionite.