Issue 12, 2006
From the journal:

Organic & Biomolecular Chemistry

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

Frances Heaney,*a   Elaine Lawless,a   Mary Mahon,b   Patrick McArdlec  and  Desmond Cunninghamc  

* Corresponding authors

a Department of Chemistry, National University of Ireland, Maynooth, Ireland

b Department of Chemistry, University of Bath, Bath, U.K.

c Department of Chemistry, National University of Ireland, Galway, Ireland

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.

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

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Article information

DOI
https://doi.org/10.1039/B602423H
Article type
Paper
Submitted
17 Feb 2006
Accepted
13 Apr 2006
First published
11 May 2006

Org. Biomol. Chem., 2006,4, 2408-2416

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

F. Heaney, E. Lawless, M. Mahon, P. McArdle and D. Cunningham, Org. Biomol. Chem., 2006, 4, 2408 DOI: 10.1039/B602423H

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