Reactions of NH 2 OH•HCl with β aroylacrylic acids proceed ambiguously: a nucleophile attacks either the carbonyl group or the C=C bond. In the latter case, the resulting α hydroxyl amino derivative converts into enamine, probably via dehydration followed by isomerization. Addition of 1,2,4 triazole to the C=C bond of β (p toluyl)acrylic acid followed by refluxing of their adduct with 60% NH 2 NH 2 •H 2 O gave a dihydropyridazinone derivative.
Scheme 1and its methyl ester 5a was unexpectedly obtained in 70% yield (Scheme 2). β Aroylacrylic acids and N nucleophiles