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    Bridgehead nitrogen heterocycles which contain the quinazoline moiety – synthesis and cycloaddition of 1,2-dihydroquinazoline 3-oxides


    Heaney, Frances and McCarthy, Tomas and Mahon, Mary and McKee, V. (2005) Bridgehead nitrogen heterocycles which contain the quinazoline moiety – synthesis and cycloaddition of 1,2-dihydroquinazoline 3-oxides. Organic & Biomolecular Chemistry, 3. pp. 4351-4361. ISSN 1477-0520

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    Abstract

    A novel synthesis of 1,2-disubstituted 1,2-dihydroquinazoline 3-oxides 8 and the first ever examples of 1,3-dipolar trapping of these nitrones to homonuclear dipolarophiles is described. The new dipoles 8 reacted with N-methyl maleimide, generating diastereomeric adducts 14–16. In the reaction between 8 and dimethyl acetylenedicarboxylate, primary cycloadducts 17 and/or stable rearrangement products, azomethine ylides 18, are formed depending on the substitution pattern of the dipole. The structure of 18c is unambiguously assigned by X-ray crystallographic analysis. An X-ray crystal structure determination is also presented for the cyclopropylisoxazoloquinazoline 22 formed by a [3 + 2] addition of 8a to 21, the dimethyl acetylenedicarboxylate tetramer.

    Item Type: Article
    Keywords: Bridgehead nitrogen heterocycles; quinazoline moiety; synthesis and cycloaddition; 1,2-dihydroquinazoline 3-oxides;
    Academic Unit: Faculty of Science and Engineering > Chemistry
    Item ID: 4291
    Depositing User: Dr. Frances Heaney
    Date Deposited: 09 Apr 2013 09:27
    Journal or Publication Title: Organic & Biomolecular Chemistry
    Publisher: Royal Society of Chemistry
    Refereed: Yes
    URI:

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