MURAL - Maynooth University Research Archive Library



    Pyrimidine annelated heterocycles—synthesis and cycloaddition of the first pyrimido[1,4]diazepine N-oxides


    Heaney, Frances and Burke, Cathriona and Cunningham, Desmond and McArdle, Patrick (2001) Pyrimidine annelated heterocycles—synthesis and cycloaddition of the first pyrimido[1,4]diazepine N-oxides. Journal of the Chemical Society, Perkin Transactions 1 (6). pp. 622-632. ISSN 0300-922X

    [img]
    Preview
    Download (345kB) | Preview


    Share your research

    Twitter Facebook LinkedIn GooglePlus Email more...



    Add this article to your Mendeley library


    Abstract

    5-Formyl- and 5-acetyl-4-(alkenylamino)pyrimidines 5 have been prepared as precursors to novel pyrimido[1,4]diazepine N-oxides 3. In addition to cyclisation to the targeted dipoles the substrates 5 have also been observed to form imidazopyrimidines 12 and 39via an intramolecular Michael addition; additionally 5b has been observed to form the pyrimidoazepinone 42. Aldonitrone 3a cycloadded readily to olefinic dipolarophiles; ketodipole 3b did not share this reactivity. Both dipoles reacted with acetylenic dipolarophiles but the ensuing cycloadducts 37 were unstable; facile ring contraction of their isoxazolopyrimidodiazepine skeletons to the pteridine nucleus is noted. The structure of 37c has been determined by X-ray crystallography.

    Item Type: Article
    Keywords: Pyrimidine; annelated heterocycles; synthesis; cycloaddition; pyrimido[1,4]diazepine N-oxides;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 7973
    Identification Number: https://doi.org/10.1039/B007163N
    Depositing User: Dr. Frances Heaney
    Date Deposited: 24 Feb 2017 16:28
    Journal or Publication Title: Journal of the Chemical Society, Perkin Transactions 1
    Publisher: Royal Society of Chemistry
    Refereed: Yes
    Funders: Enterprise Ireland (EI)
    URI:

    Repository Staff Only(login required)

    View Item Item control page

    Downloads

    Downloads per month over past year