One-pot, microwave-assisted synthesis of polymethylene-bridged bis(1H-1,2,4-triazol-5(3)-amines) and their tautomerism

Felicia Phei Lin Lim, Lee Ming Hu, Edward R.T. Tiekink, Anton V. Dolzhenko

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8 Citations (Scopus)

Abstract

A highly selective and efficient method for the synthesis of 3,3′(5,5′)-polymethylene-bis(1H-1,2,4-triazol-5(3)-amines) was developed using the reaction of dicarboxylic acids and aminoguanidine in an aqueous medium. This one-pot, microwave-promoted method was proved to be scalable affording the desired products in good yields and purity. The scope of the method was successfully explored by the preparation of a small library of polymethylene-bis(1H-1,2,4-triazol-5(3)-amines) with different alkyl chain linkers. The annular prototropic tautomerism in the prepared compounds was studied using NMR spectroscopy and X-ray crystallography.

Original languageEnglish
Pages (from-to)3792-3796
Number of pages5
JournalTetrahedron Letters
Volume59
Issue number42
DOIs
Publication statusPublished - 17 Oct 2018

Keywords

  • CIALMEYJVQCAPV-UHFFFAOYSA-N
  • Dicarboxylic acid
  • GFIDVFDVBPKVEL-UHFFFAOYSA-N
  • GNAZDVZJXQCLPG-UHFFFAOYSA-N
  • HDYKKZCPRXWZJW-UHFFFAOYSA-N
  • ITLLBMUFIIWUFW-UHFFFAOYSA-N
  • JVHWVLLANDAWPO-UHFFFAOYSA-N
  • Microwave-assisted synthesis
  • One-pot synthesis
  • RRIQYSBGTNWGDO-UHFFFAOYSA-N
  • SIDSWGCUQHPXDB-UHFFFAOYSA-N
  • Tautomerism
  • Triazole

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