Base-promoted ring-opening/recyclization of naphthoquinones to access benzo[5,6][1,4]thiazino[4,3-b]isoquinoline-7,12-diones at room temperature,Organic Chemistry Frontiers

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Base-promoted ring-opening/recyclization of naphthoquinones to access benzo[5,6][1,4]thiazino[4,3-b]isoquinoline-7,12-diones at room temperature
Organic Chemistry Frontiers ( IF 4.6 ) Pub Date : 2024-07-05 , DOI: 10.1039/d4qo00782d
Bin Tan ₁ , Zhuoqin Li ₁ , Xinlin Zhou ₁ , Chao Zhang ₁ , Guo-Jun Deng _{1,

2} , Shanping Chen ₁

Affiliation

A base-promoted nitrogen atom insertion into naphthoquinone rings to construct N-heterocycles has been described. This approach starts from easily available 2-aminobenzenethiols and 2-(indol-3-yl)naphthoquinones, affording a series of structurally valuable polycyclic heterocycles in satisfactory yields at room temperature under transition-metal-free conditions. Mechanism studies indicate that indolyl is essential for this transformation, which mediates the ring-opening and rearrangement of naphthoquinone rings.

中文翻译：

室温下碱促进萘醌开环/再环化得到苯并[5,6][1,4]噻嗪并[4,3-b]异喹啉-7,12-二酮

已经描述了碱基促进的氮原子插入萘醌环以构建N-杂环。该方法从容易获得的2-氨基苯硫醇和2-(吲哚-3-基)萘醌开始，在室温、无过渡金属的条件下以令人满意的产率提供了一系列具有结构价值的多环杂环。机理研究表明吲哚基对于这种转变至关重要，它介导萘醌环的开环和重排。

更新日期：2024-07-05

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