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Photochemical reactions of biologically important quinoxaline n oxides

Photochemical reactions of biologically important quinoxaline n oxides

Khimiko-Farmatsevticheskii Zhurnal 20(4): 399-408

The photochemical reactions of 1,4-di-N-oxides of 2,3-disubstitutional quinoxalines, among them the antibacterial preparations of quinoxidine (I) and dioxidine (II), in aprotic and hydroxyl-containing solvents have been studied and the structure of the products formed has been established by TLC, NMR1H and 13C and UV spectrophotometry. In the series of the compounds studied two types of photochemical reactions have been detected. These types proceed through different mechanisms: isomerisation with the transference of oxygen of N .fwdarw. o group and migration of the substituent to the nitrogen in heterocycle, and regrouping with the elimination of the substituent fragment and the formation of cyclic lactames. Probable structures of the intermediates forming from singlet .pi.pi.* excited states I and II have been considered. The presence of oxymethyl groups containing mobile hydroxyl protons in .alpha.-states to N .fwdarw. o functions is the principal structural factor, which determines peculiarities of the photochemical regrouping mechanism II.

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