A Tandem Ring Opening/Closure Reaction in A BF3‐Mediated Rearrangement of Spirooxindoles
A Tandem Ring Opening/Closure Reaction in A BF3‐Mediated Rearrangement of Spirooxindoles
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DOI：
10.1002/adsc.201700728
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发表时间：
2017-12
影响因子：
5.4
通讯作者：
Xuliang Guo;Qingyu Xing;Kunhua Lei;D. Zhang-Negrerie;Yunfei Du;K. Zhao
中科院分区：
文献类型：
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作者：
Xuliang Guo;Qingyu Xing;Kunhua Lei;D. Zhang-Negrerie;Yunfei Du;K. Zhao
PhI（OCOCF 3）2介导的N-取代苯甲酰苯胺的螺环化反应生成的BF 3与容易获得的螺环己二烯酮反应，引发不寻常的二烯酮-苯酚还原，生成生物学上有趣的8-羟基-菲啶-6（5 H）-酮化合物。这种独特的重排模式涉及的电子缺乏的N-甲基氨基甲酰基部分，而不是富电子的芳基基团的迁移，如以前在所有其他类似的转换中观察和报告。
Treatment of the readily accessible spiro-cyclohexadienones with BF3 from the PhI(OCOCF3)2-mediated spiro-cyclization of N-substituted benzanilides initiates an unusual dienone-phenol rearrange-ment leading to the biologically interesting 8-hydroxy-phenanthridin-6(5H)-one compounds. This unique rearrangement pattern involves the migration of the electron-deficient N-methyl carbamoyl moiety rather than the electron-rich aryl group as observed and reported previously in all other similar transformations.