Selective Preparation of Pyrrolo[2,3-c]tetrahydroquinolines and Indolo[3,2-c]tetrahydroquinolines through N-Arylation/Cycloaddition/Rearrangement Annulation Reactions of Alkynyl-Tethered Oximes with Diaryliodonium Salts

被引：1

作者：

Nie, Chang-Rui ^{[1
]}

Pan, Mei-Mei ^{[1
]}

Deng, Rong ^{[1
]}

Zhong, Xin-Xian ^{[1
]}

Chen, Chun-Hua ^{[2
]}

Mo, Dong-Liang ^{[1
]}

机构：

[1] Guangxi Normal Univ, Sch Chem & Pharmaceut Sci, Key Lab Chem & Mol Engn Med Resources, State Key Lab Chem & Mol Engn Med Resources,Minist, 15 Yu Cai Rd, Guilin 541004, Peoples R China

[2] Guangxi Minzu Univ, Sch Chem & Chem Engn, Guangxi Collaborat Innovat Ctr Chem & Engn Forest, Key Lab Chem & Engn Forest Prod,State Ethn Affairs, Nanning 530006, Peoples R China

来源：

ADVANCED SYNTHESIS & CATALYSIS | 2025年 / 367卷 / 02期

关键词：

Nitrone; Tetrahydroquinoline; 3+2] cycloaddition; Rearrangement; Diaryliodonium salts; CASCADE; TETRAHYDROQUINOLINES; CYCLIZATION; QUINOLINES; INDOLES; ACCESS; BONDS;

D O I：

10.1002/adsc.202400515

中图分类号：

O69 [应用化学];

学科分类号：

081704 ;

摘要：

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.

引用

页数：7