Highly selective scalable electrosynthesis of 4-hydroxybenzo[ e ]-1,2,4-thiadiazine-1,1-dioxides

被引：3

作者：

Winter, Johannes ^{[1
]}

Prenzel, Tobias ^{[1
]}

Wirtanen, Tom ^{[1
]}

Galvez-Vazquez, Maria de Jesus ^{[1
]}

Hofman, Kamil ^{[1
]}

Schollmeyer, Dieter ^{[1
]}

Waldvogel, Siegfried R. ^{[1
,2
,3
]}

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, Kaiserstr 12, D-76131 Karlsruhe, Germany

[3] Max Planck Inst Chem Energy Convers, Stiftstr 34-36, D-45470 Mulheim, Germany

来源：

CELL REPORTS PHYSICAL SCIENCE | 2024年 / 5卷 / 05期

基金：

瑞士国家科学基金会;

关键词：

DOPED DIAMOND ELECTRODES; N-OXIDES; ONE-POT; ELECTROCHEMICAL REDUCTION; LEADED BRONZE; DEHALOGENATION; HETEROCYCLES; INHIBITORS; OXIDATION; NITRONES;

D O I：

10.1016/j.xcrp.2024.101927

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

4 H-4-Hydroxybenzo[ e]-1,2,4-thiadiazine-1,1-dioxides are based on a widely found structural motif for pharmaceutical applications, having an additional unique exocyclic N-O bond that is not accessible by conventional synthetic routes. Electrochemistry offers a sustainable tool for the direct synthesis of these heterocyclic structures containing this N-hydroxy modification. Here, we report a highly selective synthesis of 4 H-4-hydroxybenzo[ e]-1,2,4-thiadiazine-1,1-di- oxides by direct reduction of widely available nitro arenes in almost quantitative yields. The electro-synthetic protocol is applied to more than 40 diverse examples, highlighting the versatility of this method. Furthermore, the technical relevance is demonstrated by two multi -gram -scale syntheses.

引用

页数：17

共 73 条

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