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


Reference:

Heaney, F., Lawless, E., Mahon, M., McArdle, P. and Cunningham, D., 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.

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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.

Details

Item Type Articles
CreatorsHeaney, F., Lawless, E., Mahon, M., McArdle, P. and Cunningham, D.
DOI10.1039/b602423h
DepartmentsFaculty of Science > Chemistry
RefereedYes
StatusPublished
ID Code4703
Additional InformationID number: ISI:000238129600011

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