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Synlett 1991; 1991(7): 485-486
DOI: 10.1055/s-1991-20770
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Regiospecific Synthesis of α-Alkoxy and α-Alkylthio-1-alkyl-1,2,4-triazoles from Aldehydes and Glyoxals

Keith Smith* , Andrew Small, Michael G. Hutchings
  • *Department of Chemistry, University College Swansea, Singleton Park, Swansea SA2 8PP, Wales
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Publication Date:
07 March 2002 (online)

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Reaction between aliphatic aldehydes or glyoxals (RCOCHO) and 1,2,4-triazole followed by mesyl chloride gives α-mesylates of 1-alkyl-1,2,4-triazole, regiospecifically. Mesylate ion is readily displaced by alkoxide, aryloxide, alkylthiolate, or arylthiolate nucleophiles to give the corresponding α-functionalised 1-alkyl-1,2,4-triazoles, in good yield.