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Heaney, Frances, McCarthy, Tomas, Mahon, Mary and McKee, V. (2005) Bridgehead nitrogen heterocycles which contain the quinazoline moiety – synthesis and cycloaddition of 1,2-dihydroquinazoline 3-oxides. Organic & Biomolecular Chemistry, 3. pp. 4351-4361. ISSN 1477-0520
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Abstract
A novel synthesis of 1,2-disubstituted 1,2-dihydroquinazoline 3-oxides 8 and the first ever examples of 1,3-dipolar
trapping of these nitrones to homonuclear dipolarophiles is described. The new dipoles 8 reacted with N-methyl
maleimide, generating diastereomeric adducts 14–16. In the reaction between 8 and dimethyl acetylenedicarboxylate,
primary cycloadducts 17 and/or stable rearrangement products, azomethine ylides 18, are formed depending on the
substitution pattern of the dipole. The structure of 18c is unambiguously assigned by X-ray crystallographic analysis.
An X-ray crystal structure determination is also presented for the cyclopropylisoxazoloquinazoline 22 formed by a
[3 + 2] addition of 8a to 21, the dimethyl acetylenedicarboxylate tetramer.
| Item Type: | Article |
|---|---|
| Keywords: | Bridgehead nitrogen heterocycles; quinazoline moiety; synthesis and cycloaddition; 1,2-dihydroquinazoline 3-oxides; |
| Academic Unit: | Faculty of Science and Engineering > Chemistry |
| Item ID: | 4291 |
| Depositing User: | Dr. Frances Heaney |
| Date Deposited: | 09 Apr 2013 09:27 |
| Journal or Publication Title: | Organic & 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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