Anodic and Cathodic Formation of Heterocyclic Compounds and Intermolecular Coupling by N-X Bond Formation

杂环化合物的阳极和阴极形成以及 N-X 键形成的分子间偶联

• 批准号: 352343576
• 负责人: Professor Dr. Siegfried R. Waldvogel
• 金额: --
• 依托单位: Department Elektrosynthese
• 依托单位国家: 德国
• 项目类别: Research Grants
• 资助国家: 德国
• 项目状态: 未结题
• 来源: https://gepris.dfg.de/gepris/projekt/352343576?language=en
• 关键词: Anodic; Cathodic; Formation; Heterocyclic; Compounds

The N-X bond formation holds an important key step in the synthesis of many biologically and technically relevant heterocycles. Classical methods exhibit disadvantages, such as the requirement of metals, drastic reaction conditions, and toxic reagents. Therefore, we would like to use the project funding to investigate a reaction pathway, which is safer and of higher ecological and economical sustainability, that employs electrochemical means to construct N-X bonds. Generally, electrochemistry enables two different approaches: Previously acquired experience regarding the oxidative coupling with amidyl radicals will benefit the objective to synthesize pharmaceutical and bioactive substance classes, such as indazolones, isoxazolines and isothiazoles. In addition, the involvement of multiple bonds for the synthesis of quinolones and indoles will be investigated. Furthermore, the intermolecular formation of N-N bonds will be elucidated in order to obtain important building blocks for heterocycles. The inclusion and utilization of reductive protocols for N-X bond formation completes the application spectrum of electrochemistry and provides an access point to important nitrogen heterocycles. Based on different nitro compounds, a route to substance classes such as indoles, triazoles, oxadiazoles and triazines is intended, established by inter- and intramolecular coupling.

N-X键的形成在许多生物学和技术上相关的杂环的合成中是重要的关键步骤。传统方法的缺点是需要金属，反应条件激烈，试剂有毒。因此，我们希望利用项目资金探索一种更安全、生态和经济可持续性更高的反应途径，即利用电化学手段构建N-X键。一般来说，电化学可以实现两种不同的方法：先前获得的关于与酰胺基自由基氧化偶联的经验将有助于合成药物和生物活性物质类，如吲哚酮类，异恶唑啉类和异噻唑类。此外，多键参与喹诺酮类和吲哚类化合物的合成也将被研究。此外，N-N键的分子间形成将被阐明，以获得杂环的重要组成部分。N-X键形成的还原协议的包含和利用完善了电化学的应用谱，并为重要的氮杂环提供了一个接入点。基于不同的硝基化合物，拟通过分子间和分子内偶联建立一条通往诸如吲哚、三唑、恶二唑和三嗪等物质类的途径。