A multicomponent reaction of 2-aminoimidazoles: microwave-assisted synthesis of novel 5-aza-7-deaza-adenines

Felicia Phei Lin Lim, Szy Teng Low, Elvina Lee King Ho, Nathan R. Halcovitch, Edward R.T. Tiekink, Anton V. Dolzhenko

    Research output: Contribution to journalArticleResearchpeer-review

    11 Citations (Scopus)

    Abstract

    An efficient and highly selective multicomponent synthesis of 4-aminoimidazo[1,2-a][1,3,5]triazines, which are 5-aza-7-deaza-isosteres of adenine, was developed. The reaction of 2-aminoimidazoles, triethyl orthoformate and cyanamide under microwave irradiation proceeded regioselectively to provide a library of novel 5-aza-7-deaza-adenines in good yields and purity. The developed method was demonstrated to be scalable and highly reproducible in three different monomode microwave reactors. A rearrangement was proposed to explain the high selectivity of the reaction.

    Original languageEnglish
    Pages (from-to)51062-51068
    Number of pages7
    JournalRSC Advances
    Volume7
    Issue number81
    DOIs
    Publication statusPublished - 2017

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