Английская Википедия:8-Aminoquinoline
Шаблон:Chembox Шаблон:See also 8-Aminoquinoline is the 8-amino derivative of quinoline. Often abbreviated AQ, it is a pale yellow solid. It is structurally analogous to 8-hydroxyquinoline.[1]
Drug derivatives
The derivatives primaquine, tafenoquine and pamaquine have been tested for anti-malaria activity.[2][3] Primaquine is still used routinely worldwide as part of the treatment of Plasmodium vivax and Plasmodium ovale malaria, although how it prevents malarial recurrences is not, at present, clear.[4] Tafenoquine was approved for medical use in Australia and in the United States in 2018.[5][6]
Directing group
The amine functional group is amenable to formation of amides, and thus can serve as a directing group in organic synthesis.[7][8]
Preparation
The original synthesis of AQ involved nitration of quinoline to give a mixture of the 5- and 8-nitroderivatives, which were separated by distillation and sublimation. Reduction of the 8-nitro isomer with tin powder in the presence of hydrochloric acid gave the amines.[9] AQ can also be produced by amination of 8-chloroquinoline.
References
