N-ヘテロ芳香族の電子的性状 : 第26報置換Pyrazine類およびPyrazine N-Oxide類のポーラログラ7フィー的挙動

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Polarographic behaviors of pyrazine (I), 2,5-dimethylpyrazine (II), 2,3,5,6-tetramethylpyrazine (III), 3-hydroxy-2,5-dimethylpyrazine (IV), 3-methoxy-2,5-dimethyl-pyrazine (V), 3-chloro-2,5-dimethylpyrazine (VI), 1-oxides and 1,4-dioxides of I, II, and III, and 1-oxides of IV, V, and VI at various pH values have been investigated. Whereas in acid region the polarographic waves of N-oxide groups were characteristic of diffusion as well as kinetic currents, in alkaline region they were characteristic exclusively of kinetic current, and it was presumed that at lower pH-values N-oxide group is reduced in its protonated form. In acid media, 1-oxides of I, II, and III exhibited double waves, the first of which being attributable to reduction of N-oxide groups and the second to that of the pyrazine nucleus (production of 1,4-dihydro compounds). Reduction of the two N-oxide groups of 1,4-dioxide of I proceeded simultaneously. In the case of 1-oxides of IV and V' N-oxide group and pyrazine nucleus were reduced simultaneously ; V was reduced further to piperazine compound. The cause of the different polarographic reductivities of IV and V was ascribed to a difference in their tautomeric forms. The first wave of 1-oxide of VI was attributable to reduction of the N-oxide group, and the second wave to reduction which involves hydrogenation of the nitrogen atoms of the ring and, at the same time, detachment of the chloro radical from the ring. The detachment of chlorine was confirmed further through controlled-potential electrolysis. The proposed sequences of reduction were given in charts.
社団法人日本薬学会の論文
1968-09-25

N-ヘテロ芳香族の電子的性状 : 第26報置換Pyrazine類およびPyrazine N-Oxide類のポーラログラ7フィー的挙動

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N-ヘテロ芳香族の電子的性状 : 第26報 置換Pyrazine類およびPyrazine N-Oxide類のポーラログラ7フィー的挙動

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N-ヘテロ芳香族の電子的性状 : 第26報置換Pyrazine類およびPyrazine N-Oxide類のポーラログラ7フィー的挙動