4.8 Article

Skeleton-Reorganizing Coupling Reactions of Cycloheptatriene and Cycloalkenones with Amines

期刊

出版社

WILEY-V C H VERLAG GMBH
DOI: 10.1002/anie.202213074

关键词

1; 2-Dihydroquinolines; Cycloalkenones; Cycloheptatrienes; Hydroamination; Skeleton Reorganization

向作者/读者索取更多资源

This study demonstrates a unique skeleton-reorganizing coupling reaction of cycloheptatriene and cycloalkenones with amines. The reaction selectively couples cycloheptatriene with anilines to deliver fused 1,2-dihydroquinoline products in the presence of Rh/acid catalysis. Mechanistic studies reveal that the ring reorganization occurs through retro-Mannich type ring-opening and subsequent intramolecular Povarov reaction. The synthetic utilization of this reaction is showcased with gram-scale reaction, synthetic derivatizations, and late-stage modification of commercial drugs.
Skeletal reorganization reactions have emerged as an intriguing tool for converting readily available compounds into complicated molecules inaccessible by traditional methods. Herein, we report a unique skeleton-reorganizing coupling reaction of cycloheptatriene and cycloalkenones with amines. In the presence of Rh/acid catalysis, cycloheptatriene can selectively couple with anilines to deliver fused 1,2-dihydroquinoline products. Mechanistic studies indicate that the retro-Mannich type ring-opening and subsequent intramolecular Povarov reaction account for the ring reorganization. Our mechanistic studies also revealed that skeleton-reorganizing amination between anilines and cycloalkenones can be achieved with acid. The synthetic utilization of this skeleton-reorganizing coupling reaction was showcased with a gram-scale reaction, synthetic derivatizations, and the late-stage modification of commercial drugs.

作者

我是这篇论文的作者
点击您的名字以认领此论文并将其添加到您的个人资料中。

评论

主要评分

4.8
评分不足

次要评分

新颖性
-
重要性
-
科学严谨性
-
评价这篇论文

推荐

暂无数据
暂无数据