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.
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页数：17
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