Development of the synthesis of heterocycle-fused naphthoquinones toward specific substrate for DT-diaphorase

建立了一种合成h -苯并[f]吲哚-4,9-二酮等杂环融合萘醌类化合物的简便方法。该方法采用Sonogashira偶联和串联加成消除/分子内环化技术，可在同一底物上制备多功能杂环融合萘醌类化合物。但在3位引入C1单元失败。另外，我们开发了利用铜催化的串联分子内环化/偶联反应从邻炔基苯胺合成3-取代吲哚的直接方法。此外，我们还开发了一种利用铜催化剂和分子氧作为氧化剂转化吲哚的有效方法。该转化涉及到2-芳酰吲哚的串联氧化过程。我们的反应产生了多种n -苯甲酰苯甲酸和苯并恶嗪酮。

A concise method for the synthesis of heterocycle-fused naphthoquinones such as 1H-benz[f]indole-4,9-dione was developed. This method employed Sonogashira coupling and tandem addition-elimination/intramolecular cyclization, and it enabled the preparation of versatile heterocycle-fused naphthoquinones from one substrate. However, introduction of C1 unit at 3-position was failed.Alternatively, we developed direct methods for the synthesis of 3-substituted indoles from o-alkynylanilines by utilizing a copper-catalyzed tandem intramolecular cyclization/coupling reaction.Moreover, we developed an efficient method for the transformation of indoles by utilizing a copper catalyst and molecular oxygen as the oxidant. The transformation involves a tandem oxidative process of 2-arylindoles. Our reaction afforded a variety of N-benzoyl anthranilic acids and benzoxazinones.