Catalytic and Aerobic Oxidative C-H Annulation Reactions of Saturated Cyclic Amines for Synthesis of Dipyrroloquinolines
Catalytic and Aerobic Oxidative C-H Annulation Reactions of Saturated Cyclic Amines for Synthesis of Dipyrroloquinolines
复制标题
饱和环胺催化有氧氧化 C-H 成环反应合成二吡咯并喹啉
DOI：
10.1002/adsc.202201332
复制
发表时间：
2023
影响因子：
5.4
通讯作者：
M.
中科院分区：
文献类型：
--
作者：
Matsumoto;K.; Nakano;R.; Hirokane;T.; Yamada;K.; Yoshida;M.
为了为含氮多环骨架的一步构建提供一个有效的平台，我们报道了饱和环胺的非均相铂催化氧化α,β-C(sp3)−H双官能化。该方法涉及在有氧温和条件下进行串联氧化脱氢/杂狄尔斯-阿尔德反应，以良好的产率提供四环八氢二吡咯并喹啉骨架。将该反应应用于一步合成天然产物肉桂碱B苷元和千里光联吡咯烷。这项研究以高度原子经济的方式有效、快速地获取含氮稠合四环化合物。
With the aim of providing an efficient platform for the one‐step construction of nitrogen‐containing polycyclic frameworks, we report a heterogeneous platinum‐catalyzed oxidative α,β‐C(sp3)−H dual functionalization of saturated cyclic amines. This method involves a tandem oxidative dehydrogenation/hetero Diels‐Alder reaction under aerobic mild conditions, providing tetracyclic octahydro‐dipyrroloquinoline frameworks in good yields. The reaction was applied to the synthesis of natural products incargranine B aglycone and seneciobipyrrolidine in one step. This study provides efficient and rapid access to nitrogen‐containing fused tetracyclic compounds in a highly atom‐economical fashion.