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Heaney, F,Lawless, E,Mahon, M,McArdle, P,Cunningham, D
2006
June
Organic & Biomolecular Chemistry
1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products
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Optional Fields
DIPOLAR DERIVATIVES ADDITION REACTIONS N-OXIDES 1,3-BENZODIAZEPINES DIENOPHILES SERIES
4
2408
2416
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.
DOI 10.1039/b602423h
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