quinoxaline Chem.
(kwɪˈnɒksəliːn)
[ad. G. chinoxalin (O. Hinsberg 1884, in Ber. d. Deut. Chem. Ges. XVII. 319), f. chin-olin quinoline + -oxal (f. glyoxal glyoxal) + -in -ine5. So named on account of its structural similarity to quinoline and its preparation from glyoxal.]
A weakly basic colourless crystalline solid, C8H6N2, which was first prepared by reaction of glyoxal and o-phenylenediamine, and has a bycyclic structure formed from fused benzene and pyrazine rings; any substituted derivative of this compound.
| 1884 Jrnl. Chem. Soc. XLVI. 1052 He [sc. Hinsberg]..proposes to call this series of compounds quinoxalines. The formula of quinoxaline (the lowest homologue) is undoubtedly C6H4{btr1}N:CH{bbr1}{bbr1}N:CH{btr1} . 1887 [see azine]. 1926 H. G. Rule tr. J. Schmidt's Text-bk. Org. Chem. 700 Quinoxalines..are weakly basic compounds, which may be reduced to hydro-quinoxalines, but are stable towards oxidising agents. 1951 I. L. Finar Org. Chem. x. 189 It [sc. glyoxal]..combines with o-phenylenediamines to form quinoxalines..; e.g., with o-phenylenediamine it forms quinoxaline itself. 1974 Nature 20 Dec. 654/1 The quinoxaline chromophores of echinomycin are similar in size to the quinoline chromophore of chloroquine, which is known to bind to DNA by intercalation. |