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

• Applicant: Professor Dr. Siegfried R. Waldvogel
• Subject Area: Organic Molecular Chemistry - Synthesis and Characterisation
• Term: from 2017 to 2024
• Project identifier: Deutsche Forschungsgemeinschaft (DFG) - Project number 352343576

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.

• DFG Programme: Research Grants