Dibenzofluoran and asymmetric 6′-hydroxybenzofluoran were prepared by the method reported in past literature. Other unknown compounds prepared were four asymmetric chlorinated hydroxybenzofluorans and three asymmetric chlorinated hydroxybenzofluorans. Condensation of
o-(5-chloro-2, 4-dihydroxybenzoyl) benzoic acid (II) and α- or β-naphthol, and that of
o-(3, 5-dichloro-2, 4-dihydroxybenzoyl) benzoic acid (III) with α- or β-naphthol respectively afforded 6′-hydroxy-7′-chloro-2′, 3′-benzofluoran or 6′-hydroxy-7′-chloro-3′, 4′-benzofluoran, and 5′, 7′-dichloro-6′-hydroxy-2′, 3′-benzofluoran or 5′, 7′-dichloro-6′-hydroxy-3′, 4′-benzofluoran. Direct dichlorination of tetrahydroxyfluoran gave chlorohydroxybenzofluoran.
Newly synthesized N-carboxymethylaminomethyl derivatives of 3′, 5′, 6′-, 3′, 6′, 7′-, and 3′, 6′, 8′-trihydroxy-, and 2′, 3′, 6′, 7′-, 3′, 4′, 5′, 6′-, and 1′, 3′, 6′, 8′-tetrahydroxyfluoraniminodiacetic acid, and 1′, 3′, 6′, 8′-, 2′, 3′, 6′, 7′-, and 3′, 4′, 5′, 6′-tetrahydroxyfluoranaminoacetic acid complexone compounds, which were obtained by the condensation of hydroxyfluoran and aminoacetic acid, or that of hydroxyfluoran with iminodiacetic acid and formaldehyde, following the synthetic method for 3′, 6′-dihydroxyfluoraniminodiacetic acid complexone.
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