Synthesis of Benz[f]indole-4, 9-dione Derivatives via Intramolecular Cyclization

Abstract

Benz[f]indole-4,9-dione의 구조를 가지는 화합물들은 Gram-positive bacteria에 대하여 항박테리아 작용을 갖는다고 알려져 있으므로 분자내 고리화 반응을 이용하여 새로운 benz[f]indole-4,9-dione 유도체들을 합성하였다. 2-chloro-3-(α-cyano-α-ethoxycarbonyl-methyl)-1,4-naphthoquinone에 지방족 amine류를 ethanol에서 반응시켜 2-amino-3-ethoxycarbonyl-N-alkyl-benz[f]indole-4,9-dione 유도체 Ia-f를 합성하였다. 방향족 amine류와의 반응에서는 2-arylamino-3-(α-cyano-α-ethoxycarbonyl-methyl)-1,4-naphthoquinone 유도체 IIa-h만을 얻었을 뿐, 고리화 반응은 일어나지 않았으나, 방향족 amine류의 ethanol 혼합액에 triethylamine을 촉매로 첨가하면 분자내 고리화 반응이 진행되어 2-amino-3-ethoxycarbonyl-N-aryl-benz[f]indole-4,9-dione 유도체 IIIa-f를 얻을 수 있었다.;Compounds with benz[f] indole-4,g-dione moiety are known to have an antibacterial activity against Gram-positive bacteria. The new kinds of 2-amino-benz[f] indole-4,g-diones were prepared via intramolecular cyclization. 2-Chloro-3-(a-cyano-a-ethoxycarbonyl-methyl)-1,4-naphtho- quinone was reacted with some alkylamines to yield N-alkyl-2- amino-benz [f]indole-4,9-diones (compounds Ia-f). However, when it was treated with the arylamines, only 2-amino-3-( α-cyano-α- ethoxycarbonyl-methyl)-1,4-naphthoquinones (compounds IIa-h) were obtained without furthur cyclization. The ring-closed compounds, 2-amino-3-ethoxycarbonyl-N-aryl-benz[f] indole-4,9-diones (com- pounds IIIa-f), were prepared when triethylamine was employed as a base for the reaction of 2-ch1oro-3-(α-cyano-α-ethoxycar- bonyl-methly)-1,4-naphthoquionone and arylamines.