Simple and Scalable Electrosynthesis of 1H-1-Hydroxy-Quinazolin-4-Ones
Chemical Science 2023
Olesja Koleda, Tobias Prenzel, Johannes Winter, Tomoki Hirohata, Maria de Jesus Galvez-Vazquez, Dieter Schollmeyer, Shinsuke Inagi, Edgars Sūna, Siegfried R Waldvogel

Cathodic synthesis provides sustainable access to 1-hydroxy- and 1-oxy-quinazolin-4-ones from easily accessible nitro starting materials. Mild reaction conditions, inexpensive and reusable carbon-based electrode materials, an undivided electrochemical setup, and constant current conditions characterise this method. Sulphuric acid is used as a simple supporting electrolyte as well as a catalyst for cyclisation. The broad applicability of this protocol is demonstrated in 27 differently substituted derivatives in high yields of up to 92%. Moreover, mechanistic studies based on cyclic voltammetry measurements highlight a selective reduction of the nitro substrate to hydroxylamine as a key step. The relevance for preparative applications is demonstrated by a 100-fold scale-up for gram-scale electrolysis.


DOI
10.1039/d3sc00266g
Hyperlink
https://pubs.rsc.org/en/content/articlelanding/2023/sc/d3sc00266g

Koleda, O., Prenzel, T., Winter, J., Hirohata, T., de Jesus Galvez-Vazquez, M., Schollmeyer, D., Inagi, S., Sūna, E., Waldvogel, S. Simple and Scalable Electrosynthesis of 1H-1-Hydroxy-Quinazolin-4-Ones. Chemical Science, 2023, Vol. 14, No. 10, pp.2669-2675. ISSN 2041-6520. Available from: doi:10.1039/d3sc00266g

Publication language
English (en)
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