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

Heaney, Frances
; 
Lawless, Elaine
; 
Mahon, Mary
; 
McArdle, Patrick
; 
Cunningham, Desmond
Repository DOI
Publication Date
2006-01-01
Keywords
dipolar derivatives, addition reactions, n-oxides, 1,3-benzodiazepines, dienophiles, series
Type
Article
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Citation
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
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.
Funder
Publisher
Royal Society of Chemistry (RSC)
Publisher DOI
10.1039/b602423h
Rights
Attribution-NonCommercial-NoDerivs 3.0 Ireland
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Externally hosted open access publications with University of Galway authors (1)