1,3-Dipolar character of 2-vinyl quinazoline 3-oxides; first and second generation cycloaddition products.
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.
Heaney
Frances
F
Department of Chemistry, National University of Ireland, Maynooth, Ireland.
Lawless
Elaine
E
Mahon
Mary
M
McArdle
Patrick
P
Cunningham
Desmond
D
D018360:Crystallography, X-Ray; D003500:Cyclization; D015394:Molecular Structure; D010087:Oxides / Q000138:chemical synthesis / Q000737:chemistry*; D011799:Quinazolines / Q000138:chemical synthesis / Q000737:chemistry*; D014753:Vinyl Compounds / Q000138:chemical synthesis / Q000737:chemistry*
D010087:Oxides; D011799:Quinazolines; D014753:Vinyl Compounds