벤조-[f]-인돌-4,9-디온 유도체의 합성

Synthesis of -4,9-Dione Derivatives

-4,9-dione derivatives were prepared from 2-chloro-3-(alpha-acetyl-alpha-ethoxycarbonyl-methyl)-1,4-naphthoquinone and 2-chloro-3-N-phenylamino-1,4-naphthoquinone. 2-Chloro-3-(alpha-acetyl-alpha-ethoxycarbonyl-methyl)-1,4-naphthoquinone was reacted with amines to give 2-amino-3-(a-acetyl-a-ethoxycarbonyl-methyl)-1,4-naphthoquinone derivatives. Subsequent treatment of 2-amino-3-(alpha-acetyl-alpha-ethoxycarbonyl-methyl)-1,4-naphthoquinone with sodium ethoxide gave -4,9-dione derivatives. When 2-chloro-3-N-phenylamino-1,4-naphthoquinone reacted with sodium alpha-cyano ethyl acetate, 2-amino-3-ethoxycarbonyl-N-phenyl--4,9-dione was obtained. However, with sodium diethyl malonate, not -4,9-dione but 2-chloro-3-bis-(methoxycarbonyl)-methyl-2H-3-N-phenylamino-1,4-naphthoquinone was obtained.