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Chemical and electrochemical reduction of pyrazino[2,3-g]quinoxalines and of their benz...
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Chemical and electrochemical reduction of pyrazino[2,3-g]quinoxalines and of their benzo and dibenzo derivatives; the structure of fluorindine and the formation of tetraanion
作者:
Joseph Armand,
Line Boulares,
Christian Bellec,
Jean Pinson,
期刊:
Canadian Journal of Chemistry
(NRC Available online 1987)
卷期:
Volume 65,
issue 7
页码: 1619-1623
ISSN:0008-4042
年代: 1987
DOI:10.1139/v87-271
出版商: NRC Research Press
数据来源: NRC
摘要:
The structure of fluorindine is established by nmr as the 5,14-dihydroquinoxalino[2,3-b]phenazine. The catalytic hydrogenation of 2,3-di(p-methoxyphenyl)pyrazino[2,3-b]phenazine2aleads to the 6,11-dihydro derivative4a. The electrochemical reduction in an hydroorganic medium furnishes4aand then the 1,4,6,11-tetrahydro derivative8a. In dry DMSO the voltammogram shows four monoelectronic reversible systems corresponding to the successive formation of a radical anion, dianion, radical trianion, and tetraanion. Thus2aappears as a new example of the very restricted class of compounds leading to tetraanions upon electrochemical reduction. The catalytic hydrogenation of 2,7-diphenylpyrazino[2,3-g]quinoxaline1aor the reaction of LiAlH4with 1,2,7,8-tetramethylpyrazino[2,3-g]quinoxaline1bleads to 1,2,3,4-tetrahydro compounds. The electrochemical reduction of1aand1bin hydroorganic medium leads successively to 1,4-dihydro and then to 1,4,6,9-tetrahydro compounds which undergo a further rearrangement. In dry DMSO1aand1bbehave differently from2a: one only observes two reversible monoelectronic systems.
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