Quinoxaline およびQuinoxaline N-Oxide誘導体のポーラログラフ的検討(第1報)

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Polarographic behavior of the N-O groups in 1-oxides, 4-oxides, and 1,4-dioxides of quinoxaline, 2-methylquinoxaline, 2-phenylquinoxaline, and 2-quinoxalinecarboxylic acid is discussed. The reduction wave of quinoxaline ring showed reversibility, but that of the N-O groups was found to be irreversible. Except in 2-quinoxalinecarboxylic acid 1-oxide and 1,4-dioxide, variation of pH did not show any effect on the wave height of the N-O reduction. However, the limiting current of the first reduction wave of 2-quinoxalinecarboxylic acid 1-oxide and 1,4-dioxide decreased in the neutral solutions, but the total limiting current of the first and second waves remained constant. These behaviors of the N-O groups can be interpreted by considering that the rate of proton addition to the N-O groups is very fast. By the introduction of a carboxyl, phenyl, or methyl group into the quinoxaline ring, both reductions of quinoxaline ring and the N-O group took place at more positive potentials in the order of COOH>H>C_6H_5≈CH_3. The phenyl and carboxyl groups produced a stronger effect on the reduction potentials of 1-N→O than those of 4-N→O, while a reverse effect was observed for the methyl groups. This order of facility of the N-O reduction can be correlated to the yield of synthetic N-oxidation in the reverse way. The carboxyl and phenyl derivatives of quinoxaline 1,4-dioxides showed two reduction waves due to the corresponding N-O groups, which were assigned by comparing the half-wave potential and limiting current of their monoxide derivatives, and the reduction mechanisms for these derivatives were suggested.
社団法人日本薬学会の論文
1973-02-25

Quinoxaline およびQuinoxaline N-Oxide誘導体のポーラログラフ的検討(第1報)

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