벤조-〔f〕-인돌-4, 9-디온 유도체의 합성

Abstract

2-Chloro-3-(α-acetyl-α-ethoxycarbcnyl- methyl)-1, 4-naphthoquinone과 2-chloro-3-N-phonylamino-1, 4-naphtho-quinone을 출발물질로 하여 <benzo-[f]-indole> -4, 9- dione 유도체를 합성하였다. 즉 2-Chlore-3-(α-acetyl-α-ethoxycarbonyl-methyl)-1, 4-naphthoquinone과 alkylamine 또는 arylamine류를 반응시켜 2-amino-3-(α-acetyl-α-ethoxycarbonyl- methyl)-1, 4-naphthoquinone 유도체를 만들고 여기에 염기로저 sodium ethoxide를 가해 새로운 <benzo-[f]-indole>-4, 9-dione 유도체를 합성하였다. 2-Chloro-3-N-phenylamino-1, 4- naphtho-quinone과 sodium α-cyano ethyl acetate와 반응시켜 2-amino-3-ethoxycarbonyl-N-phenyl-<benzo-[f]-indole>-4, 9-dione을 얻었다. 그러나 sodium methoxide 존재하에서 diethyl malonate를 반응시켰을 때 <benzo-[f]-indole>-4, 9-dione이 생성되지 않고 2-Chlore-3-bis-(methoxycarbonyl)-methyl-2H-3-N-phonylamino-1, 4-naphthoquinone이 생성되었다.;<Benzo-[f]-indole>-4,9-dione derivatives were prepared from 2-chloro-3-(α-acetyl-α-ethoxycarbonyl-methyl)-1,4-naphthoquinone and 2-chloro-3-N-phenylamino-1,4-naphthoquinone. 2-Chloro-3-(α-acetyl-α-ethoxycarbonyl-methyl)-1,4-naphthoquinone was reacted with amines to give 2-amino-3-(α-acetyl-α-ethoxycarbonyl-methyl)-1,4-naphthoquinone derivatives. Subsequent treatment of 2-amino-3-(α-acetyl-α-ethoxycarbonyl-methyl) -1,4-naphthoquinone with sodium ethoxide gave <benzo-[f]-indole>-4,9-dione derivatives. When 2-chloro-3-N-phenylamino-1,4-naphthoquinone reacted with sodium α-cyano ethyl acetate, 2-amino-3-ethoxycarbonyl-N-phenyl-<benzo-[f]-indole>-4,9-dione was obtained. However, with sodium diethyl malonate not <benzo-[f]-indole>-4,9-dione but 2-chloro-3-bis-(methoxycarbonyl)-methyl-2H-3-N-phenylamino-1,4-naphthoquinone was obtained.