Abstract
The addition of CH-active compounds to 6-aryl-1,2,4-triazine 4-oxide is reversible and occurs under conditions of kinetic control at position 5 of the heterocycle to form cyclic C(5)-σH adducts. Under conditions of thermodynamic control the nucleophilic attack is directed to position 3 of the heterocycle and is accompanied by its opening to form the more stable open chain addition products. Attack of ethylmagnesium bromide is directed exclusively to the 5 position of the 6-aryl-1,2,4-triazine 4-oxides as a result of the irreversibility of the given reaction.
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Kozhevnikov, D.N., Prokhorov, A.M., Rusinov, V.L. et al. Regioselectivity of Nucleophilic Attack on the Reactions of 1,2,4-Triazine 4-Oxides with Certain C-Nucleophiles. Chemistry of Heterocyclic Compounds 40, 911–915 (2004). https://doi.org/10.1023/B:COHC.0000044574.23114.58
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DOI: https://doi.org/10.1023/B:COHC.0000044574.23114.58