Synthesis of 3-(alkylamino)-, 3-(alkoxy)-, 3-(aryloxy)-, 3-(alkylthio)-, and 3-(arylthio)-1,2,4-triazines by using a unified route with 3-(methylsulfonyl)-1,2,4-triazine

In our attempts to synthesize 3-(alkylthio)- and 3-(alkoxy)-1,2,4-triazines without substituents at the 5- or 6-position, the synthesis of their anticipated precursor 3-(methylsulfonyl)-1,2,4 triazine was also optimized. The reactivity of 3-(methylsulfonyl)-1,2,4-triazine towards alkyl and aryl thiols, primary and secondary alkylamines, phenols, and alcohols was explored, and the reactions were optimized to maximize the isolation of the corresponding 3-substituted 1,2,4-triazine. Good yields were obtained for the products of the reactions with all of the aforementioned nucleophiles, with the exception of alcohols, by using alkali metal carbonates. Higher yields of 3-(alkoxy)-1,2,4-triazines were obtained by using the appropriate magnesium alkoxide as the nucleophile.