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DOI: 10.1055/a-2722-6531
1,2,3-Triazine 1-Oxides Are a Productive Platform for Synthetic Methodologies
Autoren
This work was supported by the Welch Foundation (Grant AX-1871) and the National Science Foundation (Grant 2054845).
Abstract
This graphical review provides a concise overview of the synthesis and uses of 4-carboxylato-1,2,3-triazine 1-oxides in diverse syntheses, especially of heterocyclic compounds. Prepared in high yields from reactions between vinyldiazoacetates and tert-butyl nitrite, these triazines undergo nucleophilic substitution reactions, generally at the 6-position with the loss of dinitrogen or nitrous oxide, to form diverse products. Deoxygenation to 1,2,3-triazines, inverse-electron-demand Diels–Alder reactions, borohydride-induced 1,4-hydrogen addition, and syntheses of new diazo compounds are among the new processes that have been uncovered. This review serves as an indicator for future applications.
Keywords
nucleophilic addition - heterocycles - deoxygenation - cycloaddition - inverse-electron-demand Diels–Alder reaction - triazines - diazo compoundsPublikationsverlauf
Eingereicht: 06. August 2025
Angenommen nach Revision: 15. September 2025
Accepted Manuscript online:
13. Oktober 2025
Artikel online veröffentlicht:
30. Oktober 2025
© 2025. The Author(s). This is an open access article published by Thieme under the terms of the Creative Commons Attribution License, permitting copying and reproduction so long as the original work is given appropriate credit. Contents may not be used for commercial purposes or adapted, remixed, transformed or built upon. (https://creativecommons.org/licenses/by/4.0/)
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