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

Da Hua Shi, Jitendra R. Harjani, Robert W. Gable, Jonathan B. Baell

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3 Citations (Scopus)

Abstract

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.

Original languageEnglish
Pages (from-to)2842-2850
Number of pages9
JournalEuropean Journal of Organic Chemistry
Volume2016
Issue number16
DOIs
Publication statusPublished - 1 Jun 2016

Keywords

  • Aromatic substitution
  • Nitrogen heterocycles
  • Nucleophiles
  • Oxidation
  • Synthetic methods

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