| Co-Investigator(Kenkyū-buntansha) |
KOSHITANI Jinya Nagoya Institute of Technology, Faculty of Engineering, 工学部, 助手 (50024352)
SAITO Katuhiro Nagoya Institute of Technology, Faculty of Engineering, 工学部, 助教授 (00089096)
NAN'YA Seiko Nagoya Institute of Technology, Faculty of Engineering, 工学部, 助教授 (90023100)
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| Research Abstract |
The polarographic behavior of 5H-benzo[a]phenothiazin-5-ones and its ring-substituted derivatives at a dropping mercury electrode was studied in N,N-dimethylformamide(DMF). Each compound cave well-defined two reduction waves, the half-wave potentials of which lineary corrlated with the Hammett substituent constant <sigma_p> . For the parent compound, 5H-benzo[a]phenothiazin-5-one, the similarity with the behavior of anthraquinone, the results obtained in a mixed solvent, DMF-methylcellosolve, were explained by assuming a disproportionation reaction between the parent compound and its dianion.
The iodination of quinone imines were performed in acetone. 4-Iodo-3H-phenothiazin-3-one and 6-Iodo-5H-benzo[a]phenothiazin-5-one were prepared by reacting 3H-phenothiazin-3-one or 5H-benzo[a]phenothiazin-5-one with 1,3-Iodo-5, 5-dimethylhydantoin under mild condition. Several substituted 6-anilino-5H-benzo[a]phenothazin-5-one derivatives were prepared by condensation of substituted 1,4-naphthoquinones with 2-aminobenzenethiol in pyridine. The reduction and acetylation of the resulting compounds were also investigated. The 1-substituted-5H-benzo[2,3-a]phenothiazin-5-one, 4-substituted-5H-benzo-[6,5-a]phenothiazin-5-one and 6-substituted-benzo[a][1,4]benzothiazino[3,2-c]-phenothiazine derivatives were prepared by the condensation of 5-substituted-2, 3-dichloro-1,4-naphthoquinones with 2-aminothiophenol.
The 1,6-disubstituted- and 4,6-disubstituted-11-aza-5H-benzo[a]phenoxazin-5-one as well as 6-substituted-11-aza-5H-pyrido[a]phenoxazin-5-one derivatives were preparedby condensation of 2-amino-3-hydroxy-pyridine with 5-substituted-2, 3-dichalogeno-1,4-naphthoquinones and 6,7-dibromo-5,8-quinolinequinone respectively. The resulting compounds were subjected to reduction, acetylation, dehalogenation and reaction with aniline. The 1- and 4-substituted-5H-benzo[a]-phenoxazin-5-ones were prepared by the condensation of o-aminophenol with 5-substituted-2, 3-dichloro-1,4-naphthoquinones.
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