Direct Electrochemical Synthesis of 2,3-Disubstituted Quinoline N-oxides by Cathodic Reduction of Nitro Arenes

被引：11

作者：

Winter, Johannes ^{[1
]}

Prenzel, Tobias ^{[1
]}

Wirtanen, Tom ^{[1
]}

Schollmeyer, Dieter ^{[1
]}

Waldvogel, Siegfried R. ^{[1
,2
]}

机构：

[1] Johannes Gutenberg Univ Mainz, Dept Chem, Duesbergweg 10-14, D-55128 Mainz, Germany

[2] Inst Biol & Chem Syst Funct Mol Syst IBCS FMS, Hermann Von Helmholtz Pl 1, D-76344 Eggenstein Leopoldshafen, Germany

来源：

CHEMISTRY-A EUROPEAN JOURNAL | 2023年 / 29卷 / 12期

关键词：

cyclization; electro-organic synthesis; nitrogen heterocycles; N-oxides; reduction; NEUROPATHIC PAIN; LEADED BRONZE; ELECTROSYNTHESIS; CONSTRUCTION; ANTAGONISTS; OXIDATION; EFFICIENT; CORROSION;

D O I：

10.1002/chem.202203319

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

The use of electric current in synthetic organic chemistry offers a sustainable tool for the selective reductive synthesis of quinoline N-oxides starting from easily accessible nitro compounds. The reported method employs mild and reagent-free conditions, a simple undivided cell, and constant current electrolysis set-up which provides conversion with a high atom economy. The synthesis of 30 differently substituted quinoline N-oxides was successfully performed in up to 90 % yield. Using CV studies, the mechanism of the selective formation of the quinoline N-oxides was elucidated. The technical relevance of the described reaction could be shown in a 50-fold scale-up reaction.

引用

页数：7

共 53 条

[21] Counter Electrode Reactions-Important Stumbling Blocks on the Way to a Working Electro-organic Synthesis [J].