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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    5 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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