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Issue 12, 2006
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1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products

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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.

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

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Publication details

The article was received on 17 Feb 2006, accepted on 13 Apr 2006 and first published on 11 May 2006


Article type: Paper
DOI: 10.1039/B602423H
Citation: Org. Biomol. Chem., 2006,4, 2408-2416
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    1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products

    F. Heaney, E. Lawless, M. Mahon, P. McArdle and D. Cunningham, Org. Biomol. Chem., 2006, 4, 2408
    DOI: 10.1039/B602423H

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