Addition reactions O 0060Reactions of β-Aroylacrylic Acids with N-Nucleophiles. -The title reactions can follow alternative pathways, i.e. attack of the nucleophile on either the carbonyl group or the C=C double bond. -(KHACHIKYAN, R. D.; KARAMYAN*, N. V.; PANOSYAN, H. A.; INJIKYAN, M. H.; Russ.
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
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