通过氧化偶联重排实现四氢-β-咔啉或四氢-γ-咔啉的多样化功能化。
Diverse Functionalization of Tetrahydro-β-carbolines or Tetrahydro-γ-carbolines via Oxidative Coupling Rearrangement.
机构信息
College of Chemistry, Fuzhou University, Fuzhou, Fujian 350116, China.
出版信息
J Org Chem. 2021 Jan 1;86(1):794-812. doi: 10.1021/acs.joc.0c02351. Epub 2020 Nov 24.
We report herein diverse functionalization of tetrahydro-β-carbolines (THβCs) or tetrahydro-γ-carbolines (THγCs) via oxidative coupling rearrangement. The treatment of THβCs or THγCs with -BuOOH (TBHP) afforded 3-peroxyindolenines, followed by HCl catalyzed indolation to form unexpected 2-indolyl-3-peroxyindolenines. Further rearrangement of these peroxides allows for rapid access to a skeletally diverse chemical library in good to excellent yields.
我们在此报告了通过氧化偶联重排对四氢-β-咔啉（THβCs）或四氢-γ-咔啉（THγCs）进行的各种功能化。用 -BuOOH（TBHP）处理 THβCs 或 THγCs 可得到 3-过氧吲哚啉，然后在 HCl 催化下吲哚化形成意想不到的 2-吲哚基-3-过氧吲哚啉。这些过氧化物的进一步重排可以快速获得骨架多样的化学文库，产率良好至优秀。
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