A new one-pot three-component synthesis of 4-Aryl-6-cycloamino-1,3,5-triazin-2-amines under microwave irradiation

Muhammad Syafiq Bin Shahari, Ahmad Junaid, Edward R.T. Tiekink, Anton V. Dolzhenko

    Research output: Contribution to journalArticleResearchpeer-review

    Abstract

    A new method for the fast synthesis of diverse 4-aryl-6-cycloamino-1,3,5-triazin-2-amines was developed. The synthesis is performed under microwave irradiation in a one-pot manner from cyanoguanidine, aromatic aldehydes, and cyclic amines. Their three-component reaction in the presence of hydrochloric acid produced dihydrotriazines, which were then converted (without isolation) into the targeted compounds via aromatic dehydrogenation in the presence of alkali. The reaction tolerated various aromatic aldehydes (including heterocyclic) and cyclic amines. Crystal structures of two representative 4-aryl-6-morpholino-1,3,5-triazin-2-amines were established by X-ray crystallography. The results of preliminary biological screening identified potent antileukemic activity for 6-[3,4-dihydroisoquinolin-2(1 H)-yl]-4-phenyl-1,3,5-triazin-2-amine.

    Original languageEnglish
    Pages (from-to)2457-2468
    Number of pages12
    JournalSynthesis
    Volume53
    Issue number14
    DOIs
    Publication statusPublished - 20 Jul 2021

    Keywords

    • antiproliferative activity
    • dehydrogenative aromatization
    • microwave-assisted synthesis
    • multicomponent reactions
    • triazines

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