Nitroquinolineと次亜臭素酸ナトリウム溶液の反応(第2報) : 2-, 4-, 5-, 6-及び8-Nitroquinoline(有機化学)

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An addition-elimination reaction, which was reported in the reaction of 3-nitroquinoline with aqueous sodium hypobromite in methanolic KOH, also occurred in the case of other nitroquinolines, i.e., 6-, 5-, 8-, and 4-nitroquinolines. 6-Nitroquinoline (I) gave 6-bromo-5-methoxyquinoline (IIa), 6,8-dibromo-5-methoxyquinoline (IIb), 6-bromo-5,7-dimethoxyquinoline (IIIa), 5,7-dimethoxy-6-nitroquinoline (IIIb), 8-bromo-5,7-dimethoxy-6-nitroquinoline (IIIc), and 8-bromo-6-oxo-5,5,7-trimethoxy-5,6-dihydroquinoline (IV) on being reacted in the same way as in the reaction of 3-nitroquinoline. Other nitroquinolines and their products from the same reaction were ; 5-nitroquinoline (XI); 5-bromo-6-methoxyquinoline (XIIa), 6-methoxy-5-nitroquinoline (XIIb), 8-methoxy-5-nitroquinoline (XIIIa), 5,7-dibromo-6,8-dimethoxyquinoline (XIVa), and 6,8-dimethoxy-5-nitroquinoline (XIVb). 8-Nitroquinoline (XVIII); 8-bromo-7-methoxyquinoline (XIX), 5-methoxy-8-nitroqninoline (XX), and 6-bromo-5,7-dimethoxy-8-nitroquinoline (XXI). 4-Nitroquinoline (XXII); 4-bromo-3-methoxyquinoline (XXIIIa), 3-methoxy-4-nitroquinoline (XXIIIb), 2,3-dimethoxy-4-nitroquinoline (XXIV) and 4-methoxyquinoline (XXV). The reaction of 2-nitroquinoline (XXX) gave only 2-methoxyquinoline (XXXI).
公益社団法人日本薬学会の論文
1972-02-25

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