Anhydrous Hydrogen Iodide-Mediated Reductive Indolization of In Situ-Generated Cyclopropyl Hydrazones
Anhydrous Hydrogen Iodide-Mediated Reductive Indolization of In Situ-Generated Cyclopropyl Hydrazones
复制标题
无水碘化氢介导的原位生成环丙基腙的还原吲哚化反应
DOI：
10.1021/acs.orglett.1c03607
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发表时间：
2021
期刊：
影响因子：
5.2
通讯作者：
Ueda Masafumi
中科院分区：
文献类型：
--
作者：
Yasui Motohiro;Fujioka Hiroki;Takeda Norihiko;Ueda Masafumi
本文报道了N-芳基-C-环丙基腙的Fischer型原位吲哚化反应，然后用叔丁基碘作无水HI发生剂进行化学选择性还原。该方案提供了带有羧酸衍生物单元的吲哚。一系列对照实验表明HI介导的螺环丙基吲哚啉的形成和还原。无水HI既可作为布朗斯台德酸，也可作为还原剂，促进不稳定反应中间体和碘化混合物在平衡状态下的成功转化。
Fischer-type indolization ofN-aryl-C-cyclopropyl hydrazones generated in situ followed by chemoselective reduction usingtert-butyl iodide as an anhydrous HI generator was developed. This protocol provides indoles bearing carboxylic acid derivative units. A series of control experiments indicated the HI-mediated formation and reduction of spirocyclopropyl indolenines. Anhydrous HI functions as a Brønsted acid as well as a reducing agent, facilitating the successful conversion of unstable reaction intermediates and iodinated mixtures in equilibrium.