Photochemical substitution of methoxyanthraquinones with amines and other nucleophiles
Photochemical substitution of methoxyanthraquinones with amines and other nucleophiles
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甲氧基蒽醌与胺和其他亲核试剂的光化学取代
DOI：
10.1039/p19740002283
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发表时间：
1975
期刊：
影响因子：
--
通讯作者：
C. Hawkins
中科院分区：
文献类型：
--
作者：
J. Griffiths;C. Hawkins
1-甲氧基蒽醌与氨水和伯脂肪胺发生光化学亲核取代反应，得到高产率的1-氨基或1-烷基氨基-蒽醌。仲胺和伯芳胺不发生反应。某些无机亲核试剂也观察到了光取代作用。2-甲氧基-2-甲氧基-蒽醌的活性较低，但可以与氨光化学取代得到2-氨基和1-氨基-2-甲氧基-蒽醌，其相对比例取决于反应过程中氧气的可用性。初级脂肪胺和无机亲核试剂的光反应效率较低。讨论了这些反应的合成意义。
1-Methoxyanthraquinone undergoes photochemical nucleophilic substitution with ammonia and primary aliphatic amines to give good yields of the 1-amino- or 1-alkylamino-anthraquinone. The reaction does not occur with secondary amines and primary arylamines. Photosubstitution is also observed with certain inorganic nucleophiles. 2-Methoxyanthraquinone is less reactive, but undergoes photochemical substitution with ammonia to give 2-amino- and 1-amino-2-methoxy-anthraquinone, the relative proportions depending on the availability of oxygen during the reaction. Less efficient photoreactions occur with primary aliphatic amines and inorganic nucleophiles. The synthetic implications of these reactions are discussed.