New one-pot synthesis of 1,3,5-triazines: Three-component condensation, dimroth rearrangement, and dehydrogenative aromatization

Ahmad Junaid, Felicia Phei Lin Lim, Edward R.T. Tiekink, Anton V. Dolzhenko

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    12 Citations (Scopus)

    Abstract

    A new, effective one-pot synthesis of the 6,N2-diaryl-1,3,5-triazine-2,4-diamines under microwave irradiation was developed. The method involved an initial three-component condensation of cyanoguanidine, aromatic aldehydes, and arylamines in the presence of hydrochloric acid. Without isolation, the resulting 1,6-diaryl-1,6-dihydro-1,3,5-triazine-2,4-diamines were treated with a base to initiate Dimroth rearrangement and spontaneous dehydrogenative aromatization, affording the desired compounds. The developed method was found to be sufficiently general in scope, tolerating various aromatic aldehydes and amines; by using their combinations in the first step, a representative library of 110 compounds was successfully prepared and screened for anticancer properties.

    Original languageEnglish
    Pages (from-to)548-555
    Number of pages8
    JournalACS Combinatorial Science
    Volume21
    Issue number7
    DOIs
    Publication statusPublished - 8 Jul 2019

    Keywords

    • anticancer activity
    • microwave-assisted synthesis
    • multicomponent reactions
    • triazines

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