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

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

Research output: Contribution to journalArticle

10 Citations (Scopus)

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.
Original languageEnglish
Pages (from-to)2408-2416
Number of pages9
JournalOrganic and Biomolecular Chemistry
Volume4
Issue number12
DOIs
Publication statusPublished - 2006

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