Abstract
Treatment of secondary and tetriary succinamic acids with acetic anhydride and perchloric acid gave succinisoimidium perchlorates (5), which reacted with primary and secondary amines to yield NN′-substituted succinamides. The deprotonation of tertiary and secondary succinisoimidium salts was investigated and evidence for the formation of unstable N-phenyl- and N-t-butyl-succinisoimides was obtained. Six phthalisoimidium perchlorates (11) were prepared; their reactions with nucleophiles are described. Stable phthalisoimides, obtained from secondary phthalisoimidium perchlorates, were studied. In the homophthalic acid series, five 3-ammonio-3,4-dihydro-1H-2-benzopyran-1-one perchlorates (27) were prepared, which yielded N-substituted 3-amino-1H-2-benzopyran-1-ones (28) on deprotonation. An isomeric homophthalisoimidium salt, 3,4-dihydro-1-morpholinio-1H-2-benzopyran-3-one perchlorate (32), was synthesised. Isoimidium salts derived from αα′-diphenylsuccinic, maleic, cyclopropane-1,2-dicarboxylic, and diphenic acid were obtained. 1,2-Dihydro-2-dimethylammonio-3,1-benzoxazin-4-one perchlorate (47) was converted into 2-dimethylamino-3,1-benzoxazin-4-one (48).
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