2,3-Triazine 1-Oxides are a Productive Platform for Synthetic Methodologies

This graphical review provides a concise overview of the synthesis and uses of 4-carboxylato-1,2,3triazine 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.