We describe a selective preparation of a variety of functionalized pyrrolo[2,3‐c]tetrahydroquinolines and indolo[3,2‐c]tetrahydroquinolines in 40‐82% and 40‐80% yields from alkynyl‐tethered oximes with diaryliodonium triflates, respectively. The one‐pot reaction underwent N‐arylation, intramolecular [3+2] cycloaddition, selective [1.3] or [3,3]‐rearrangement of N‐O bond in total three steps. Experimental studies revealed that EtOAc solvent and copper(II)‐catalyst played crucial roles on the formation of these two tetrahydroquinoline scaffolds. Moreover, these two tetrahydroquinoline scaffolds could be converted into various tetrahydroquinoline building blocks by further transformations.

中文翻译：

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通过炔基拴系肟与二芳基二烯铵盐的 N-芳基化/环加成/重排环化反应选择性制备吡咯并[2,3-c]四氢喹啉和吲吲[3,2-c]四氢喹啉


我们描述了各种官能化吡咯并[2,3-c]四氢喹啉和吲哚[3-2-c]四氢喹啉的选择性制备，分别以 40-82% 和 40-80% 的产率从烷基系肟与二芳基二氟啶的三氟甲酸酯中得到。一锅反应总共经历了 N-芳基化、分子内 [3+2] 环加成反应、N-O 键的选择性 [1.3] 或 [3,3] 重排。实验研究表明，EtOAc 溶剂和铜 （II） 催化剂在这两个四氢喹啉支架的形成中起关键作用。此外，这两个四氢喹啉支架可以通过进一步的转化转化为各种四氢喹啉构建单元。