Facile synthesis of 6-cyano-9-substituted-9H-purines and their ring expansion to 8-(arylamino)-4-imino-3-methylpyrimidino-[5,4-d]pyrimidines

A. Al-Azmi, B. L. Booth, R. A. Carpenter, A. Carvalho, E. Marrelec, R. G. Pritchard, M. Fernanda, J. R P Proença

    Research output: Contribution to journalArticlepeer-review

    Abstract

    6-Cyano-9-substituted-9H-purines were prepared in a high yielding, one-step process by refluxing triethyl orthoformate or triethyl orthopropionate with the corresponding (Z)-N1-(aryl- or benzyl)-N2-(2-amino-1,2-dicyanovinyl)formamidines. Attempted reaction of these cyanopurines with aqueous methylamine furnished 8-(arylamino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidines, by attack at the imidazole ring rather than addition to the 6-cyano group. All compounds have been fully characterised by spectroscopic data and an X-ray crystal structure determination has been carried out on the 8-(4-methoxyanilino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidine.
    Original languageEnglish
    Pages (from-to)2532-2537
    Number of pages5
    JournalJournal of the Chemical Society. Perkin Transactions 1
    Issue number20
    DOIs
    Publication statusPublished - 2001

    Keywords

    • Crystal structure; Molecular structure (of 8-(4-methoxyanilino)-4-imino-3-methylpyrimidino[5,4-d]pyrimidine); Ring enlargement (prepn. and ring-expansion of cyanopurines)

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