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    1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products


    Heaney, Frances and Lawless, Elaine and Mahon, Mary and McArdle, Patrick and Cunningham, Desmond (2006) 1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products. Organic and Biomolecular Chemistry, 4 (12). pp. 2408-2416. ISSN 1477-0520

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    Abstract

    The reaction between the heteroaromatic N-oxides 1a, 1b and 1c with dimethyl acetylenedicarboxylate or methyl propiolate furnishes 1,3-benzodiazepines, the products of ring transformations of primarily formed cycloadducts. The structures of 8a and 10a have been confirmed by X-ray crystallographic analysis. The aldonitrone 1c also reacts with N-methylmaleimide and with phenyl vinyl sulfone to furnish the first examples of primary cycloaddition products from quinazoline 3-oxides.

    Item Type: Article
    Keywords: 1,3-Dipolar character; 2-vinyl quinazoline 3-oxides; cycloaddition products;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 7963
    Identification Number: https://doi.org/10.1039/B602423H
    Depositing User: Dr. Frances Heaney
    Date Deposited: 24 Feb 2017 16:33
    Journal or Publication Title: Organic and Biomolecular Chemistry
    Publisher: Royal Society of Chemistry
    Refereed: Yes
    URI:

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