Chemical and Pharmaceutical Bulletin
Online ISSN : 1347-5223
Print ISSN : 0009-2363
ISSN-L : 0009-2363
Studies on 4-Hydroxyaminoquinoline 1-Oxide and Its Related Compounds. Synthesis of 3-Chloro-and 3-Bromo-4-aminoquinoline 1-Oxide and Presentation of Chemical Evidence for a New Type of Aromatic Rearrangement of N, O-Diarylhydroxylamines
澤西 啓之神谷 庸
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ジャーナル フリー

1975 年 23 巻 11 号 p. 2949-2957

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The present paper deals with thermolyses of 4-hydroxyaminoquinoline 1-oxide (4HAQO) in acidic media and a new type of rearrangement of N, O-diarylhydroxylamine derived from 4HAQO and 4-hydroxyaminoquinoline. Thermolyses of 4-hydroxyaminoquinoline or-pyridine derivatives in hydrochloric or hydrobromic acid gave corresponding 3-halo-4-amino derivatives in relatively high yield. It was also found that N, O-di(4-quinolyl) hydroxylamine and N-(4-quinolyl)-O-(2, 4-dinitrophenyl) hydroxylamine were rearranged to a corresponding diaryl derivative, 3, 3'-(4-amino-4'-hydroxy) biquinoline and 3-(2'-hydroxy-3', 5'-dinitrophenyl)-4-aminoquinoline, respectively. Those facts presented the first chemical evidences for an aromatic rearrangement of N, O-diarylhydroxylamine which had already been predicted by Dewar.
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© The Pharmaceutical Society of Japan
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