Heaney, Frances and Lawless, Elaine and Mahon, Mary and McArdle, Patrick and Cunningham, Desmond (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. ISSN 1477-0520

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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.

Item Type:	Article
Keywords:	1,3-Dipolar character; 2-vinyl quinazoline 3-oxides; cycloaddition products;
Academic Unit:	Faculty of Science and Engineering > Chemistry
Item ID:	7963
Identification Number:	https://doi.org/10.1039/B602423H
Depositing User:	Dr. Frances Heaney
Date Deposited:	24 Feb 2017 16:33
Journal or Publication Title:	Organic and Biomolecular Chemistry
Publisher:	Royal Society of Chemistry
Refereed:	Yes
URI:	http://pubs.rsc.org
Use Licence:	This item is available under a Creative Commons Attribution Non Commercial Share Alike Licence (CC BY-NC-SA). Details of this licence are available here

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