Syntheses of Heterocyclic Compounds of Nitrogen. CX. Azaphenoxazine Derivatives.
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概要
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3-Bromo-4-(o-hydroxyphenylamino)-5-nitropyridine prepared from the potassium salt of o-aminophenol and 3-bromo-4-chloro-5-nitropyridine easily yielded 4-nitro-5H-benzo [b] pyrido [4,3-e]-1,4-oxazine by the intramolecular condensation in the presence of piperidine or potassium hydroxide. Attempts to prepare a ring-fused azaphenoxazine from the potassium salts of o-aminophenol and 2-chloro-3,5-dinitropyridine in alkaline medium ended in failure, only giving 2-(o-hydroxyphenylamino)-3,5-dinitropyridine. On the other hand, when 2-chloro-3,5-dinitropyridine was allowed to react with o-methylaminophenol, 3-nitro-10-methylbenzo [e] pyrido [3,2-b]-1,4-oxazine was obtained. These facts are well explainable from the hypothesis of a chelate ring formation forwarded by Brady. 3-Amino-5-chloro-2-pyridone was condensed with s-trinitroanisole giving 3-chloro-6,8-dinitro-5H-benzo [b] pyrido [3,2-e]-1,4-oxazine.
- 公益社団法人日本薬学会の論文
- 1958-02-20
著者
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米田 文郎
Pharmaceutical Sciences, Kumamoto University
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高橋 酉蔵
Pharmaceutical Institute Medical Faculty University Of Kyoto And Gifu College Of Pharmacy
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