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Heaney, Frances, Lawless, Elaine, Mahon, Mary, 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: | 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 |
| Related URLs: | |
| 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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