Simple electrochemical synthesis of cyclic hydroxamic acids by reduction of nitroarenes

The electrochemical reduction of nitroarenes allows direct access to manifold nitrogen containing heterocycles. This work reports the simple and direct electro-organic synthesis of 18 different examples of 2 H ,4 H -4-hydroxy-1,4-benzoxazin-3-ones in up to 81% yield. The scalability of the method wa...

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Bibliographic Details
Published in:Chemical communications (Cambridge, England) England), 2024-07, Vol.6 (55), p.765-768
Main Authors: Winter, Johannes, Lühr, Susan, Hochadel, Kyra, Gálvez-Vázquez, María de Jesús, Prenzel, Tobias, Schollmeyer, Dieter, Waldvogel, Siegfried R
Format: Article
Language:English
Subjects:
Chemical reduction
Chemical synthesis
Chemistry
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Summary:The electrochemical reduction of nitroarenes allows direct access to manifold nitrogen containing heterocycles. This work reports the simple and direct electro-organic synthesis of 18 different examples of 2 H ,4 H -4-hydroxy-1,4-benzoxazin-3-ones in up to 81% yield. The scalability of the method was demonstrated on a gram-scale. A simple and scalable electrosynthesis of a broad scope of 4-hydroxy-1,4-benzoxazin-3-ones was developed by simple reduction of inexpensive nitroarenes.
ISSN:1359-7345
1364-548X
1364-548X
DOI:10.1039/d4cc02118e