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Synthesis of 1-amino- and 1-hydroxy-9,10-anthraquinone derivatives based on reaction sequences between 2-acetyl-1,4-naphthoquinone and enamines

✍ Scribed by Kazuhiro Kobayashi; Masaharu Uchida; Shinya Watanabe; Atsushi Takanohashi; Miyuki Tanmatsu; Osamu Morikawa; Hisatoshi Konishi

Publisher: Elsevier Science
Year: 2000
Tongue: French
Weight: 141 KB
Volume: 41
Category: Article
ISSN: 0040-4039
DOI: 10.1016/s0040-4039(00)00168-4

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✦ Synopsis

2-Acetyl-1,4-naphthoquinone was treated with pyrrolidine (or morpholine) enamines, derived from cyclic and acyclic ketones, in DMF at room temperature for 24-72 h to afford 3,4-disubstituted 1-pyrrolidino(or morpholino)-9,10-anthraquinones. On the other hand, when the treatment of 2-acetyl-1,4-naphthoquinone with enamines for 2 min was followed by addition of water and heating at 100°C for 2 h, the corresponding 1-hydroxy-9,10naphthoquinone derivatives were obtained.

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