Reactions of 3-acetyltropolone and its methyl ethers with o-aminophenol.
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概要
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3-Acetyltropolone (<B>1</B>) and 2-acetyl-7-methoxytropone (<B>2a</B>) reacted with <I>o</I>-aminophenol in ethanol to afford 2-acetyl-7-(<I>o</I>-hydroxyanilino)tropone (<B>3</B>). The reaction of 3-acetyl-2-methoxytropone (<B>2b</B>) gave <B>3</B>-acetyl-2-(<I>o</I>-hydroxyanilino)tropone (<B>5</B>). The compounds <B>3</B> and <B>5</B> were cyclized to 6-acetyl- and 10-acetylcyclohepta[<I>b</I>][1,4]benzoxazines (<B>4</B> and <B>6</B>), respectively, by heating their acetic acid solutions in the presence of a trace amount of concentrated sulfuric acid. The compounds <B>4</B> and <B>6</B> were also obtained directly from <B>1</B> (or <B>2a</B>) and <B>2b</B>, respectively, by the reaction with <I>o</I>-aminophenol in acetic acid. The compound <B>5</B> exists as a tautomeric mixture with <B>5</B>′.
- 公益社団法人 日本化学会の論文
著者
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IMAFUKU Kimiaki
Department of Chemistry, Faculty of Science, Kumamoto University
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Ogura Makoto
Department of Chemistry, Faculty of Science, Kumamoto University
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Shigenobu Akihiro
Department of Chemistry, Faculty of Science, Kumamoto University
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