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