Unexpected ring contraction and oxidation rearrangement reactions of securinine

详细信息	查看全文 | 推荐本文 |

• 作者：Jun-Yong Li^&dagger ; ; Bing-Xin Zhao^&dagger ; ; Wen Zhang ; Chen Li ; Xiao-Jun Huang ; Ying Wang ; ^{wangying_cpu@163.com} ; Ping-Hua Sun ; Wen-Cai Ye ; Wei-Min Chen ; ^{twmchen@jnu.edu.cn}
• 关键词：Securinine ; Rearrangement ; Ring-contraction ; Oxidation
• 刊名：Tetrahedron
• 出版年：2012
• 期刊代码：107_00404020
• 类别：ch
• 出版时间：27 May, 2012
• 卷：68
• 期：21
• 页码：3972-3979
• 文件大小：796 K

摘要

The bromination and oxidation of securinine were studied. An interesting and surprising rearrangement was observed during the reaction of securinine with tribromo-isocyanuric acid or 1,3-dibromo-5,5-dimethylhydantoin in methanol, yielding a stereoselective ring contraction norsecurinine derivative. Meanwhile two oxidation rearrangement products were also reported. Some preliminary discussions on the reactivity of securinine were conducted from these rearrangements; it is believed to be induced by alkaline nitrogen atom of the molecule.