芳香族複素環化合物の反応機構(第11報) : Nitroquinolineと次亜臭素酸ナトリウム溶液の反応(第1報) : 3-Nitroquinoline(有機化学)

概要

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3-Nitroquinoline (I) was reacted with aqueous sodium hypobromite in methanolic KOH at definite temperature (37-40° for condition A, 0-5° for condition B, and -40--35° for condition C). The products obtained under these conditions were 3-bromo-4-methoxyquinoline (IIa), 3,6,8-tribromo-4-methoxyquinoline (IIb), 3-bromo-2,4-dimethoxyquinoline (IIIa), 3,6-dibromo-2,4-dimethoxyquinoline (IIIb), 3,6,8-tribromo-2,4-dimethoxyquinoline (IIIc), 2,4-dimethoxy-3-nitroquinoline (IVa), 6-bromo-2,4-dimethoxy-3-nitroquinoline (IVb), 2,4,6-tribromoaniline (Va), and 2,4,6-tribromo-3-methoxyaniline (Vb). Similarly, the reaction of 2-alkoxy-3-nitroquinoline (VII, 2-CH_3O, VIII, 2-C_2H_5O) gave 2-alkoxy-3-bromo-4-methoxyquinoline (IIIa ; IX) and 2-alkoxy-4-methoxy-3-nitroquinoline (IVa ; X). The same reaction of 2-alkoxy-4-methoxy-3-nitroquinoline (IVa, 2-CH_3O, X, 2-C_2H_5O) gave 2-alkoxy-3-bromo-3,4-dihydro-4,4-dimethoxy-3-nitroquinoline (XI ; XII). This reaction was discussed as an addition-elimination mechanism involving CH_3O^- addition at the 4-position of I, followed by bromination at the 3-position and elimination of HNO_2 o HBr.
公益社団法人日本薬学会の論文
1972-02-25