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題 名 | 2,3,7-Triazabicyclo[3.3.0]octenes Prepared by Tandem Cascade Reaction of Allyl Azides and Olefinic Dipolarophiles |
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作 者 | 楊嘉喜; 沈宏章; 王瑞諠; 王如春; | 書刊名 | Journal of the Chinese Chemical Society |
卷 期 | 49:1 2002.02[民91.02] |
頁 次 | 頁95-102 |
分類號 | 346.01 |
關鍵詞 | Allyl azide; Cycloaddition; Diazo compounds; Isomerization; Bicyclic heterocyclic compounds; Tandem cascade reaction; One-pot reaction; |
語 文 | 英文(English) |
英文摘要 | Tandem cascade reactions of allyl azides and olefinic dipolarophiles to give cis-fused 2,3,7-triazabicyclo[3.3.0]octenes (5, 6 or 7) are reported. Therein, an intermolecular dipolar cycloaddition of azide and alkene gave a triazoline which was followed by isomerization of the triazoline to a diazo ester (4) and then an intramolecular dipolar cycloaddition from the diazo functional group and the double bond in 4 to give 5. Compound 5 may furthermore undergo a Michael addition to give 7-substituted-2,3,7-triazabicyclo[3.3.0]oct-2-ene (6) or a tautomerization to give 2,3,7-triazabicyclo[3.3.0]oct-3-ene (7). The reaction may be manipulated to stop at a particular stage by adopting a suitable solvent or an appropriate temperature. |
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