Formal [4+2]‐Annulation of Vinyl Azides with N‐Unsaturated Aldimines |
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| Authors: | Xu Zhu Dr Yi‐Feng Wang Feng‐Lian Zhang Prof Shunsuke Chiba |
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| Institution: | Division of Chemistry and Biological Chemistry, School of Physical and Mathematical Sciences, Nanyang Technological University, Singapore 637371 (Singapore), Fax: (+65)?6791‐1961 |
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| Abstract: | Highly functionalized quinolines and pyridines could be synthesized by BF3?OEt2‐mediated reactions of vinyl azides with N‐aryl and N‐alkenyl aldimines, respectively. The reaction mechanism could be characterized as formal 4+2]‐annulation, including unprecedented enamine‐type nucleophilic attack of vinyl azides to aldimines and subsequent nucleophilic cyclization onto the resulting iminodiazonium ion moieties. |
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| Keywords: | annulation azides heterocycles Lewis acids |
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