One-Step Construction of Tetrahydro-5H-indolo[3,2-c]quinolines from Benzyl Azides and Indoles via a Cascade Reaction Sequence

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• 作者：Zengqiang Song ; Yu-Ming Zhao ; Hongbin Zhai
• 刊名：Organic Letters
• 出版年：2011
• 出版时间：December 16, 2011
• 年：2011
• 卷：13
• 期：24
• 页码：6331-6333
• 全文大小：677K
• 年卷期：v.13,no.24(December 16, 2011)
• ISSN：1523-7052

文摘

A novel one-step assembly of tetrahydro-5H-indolo[3,2-c]quinolines from benzyl azides and indoles via a formal [4 + 2] cycloaddition is described. A cascade reaction sequence, which involves benzyl azide-to-iminium rearrangement followed by two sequential Pictet鈥揝pengler reactions, generates the tetracycles in moderate to excellent yields. The current method is applicable to a broad substrate scope and holds significant potential in constructing polycyclic indolines with tertiary and/or quaternary carbon centers.