Cyclohepta[b][1,4]benzothiazines and their diazine analogues. 2. Formation and properties of cyclohepta[b]quinoxalines.
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概要
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2-Chloro- or 2-methoxytropone reacts with <I>o</I>-phenylenediamine to give 2-(<I>o</I>-aminoanilino)tropone, which upon heating provides 6<I>H</I>-cyclohepta[<I>b</I>]quinoxaline (<B>10a</B>). Upon acidification, <B>10a</B> reversibly gives a green cation, <B>9a</B>. <B>10a</B> is easily converted, especially under basic conditions, into the oxidative dimer <B>16a</B>, which reproduces <B>9a</B> by reduction with Zn in acetic acid. The isopropyl derivatives of these compounds are prepared by the same method from 5-isopropyl-2-methoxytropone. The 5-methyl (<B>21a</B>) and 5,11-dimethyl derivatives <B>23</B> are made by the reaction of 2-chloro- or 2-methoxytropone with <I>N</I>-methyl- and <I>N</I>,<I>N</I>′-dimethyl-<I>o</I>-phenylenediamines. However, the methylation of <B>21a</B> with methyl fluorosulfate affords 5,11-dihydro-8,11-dimethyl-6<I>H</I>-cyclohepta[<I>b</I>]quinoxaline-5,6-sultone. H<SUB>2</SUB>O<SUB>2</SUB> oxidation of <B>10a</B> mainly gives <B>16a</B> in addition to a small quantity of 6<I>H</I>-cyclohepta[<I>b</I>]quinoxalin-6-one. Compound <B>21a</B> is stable under basic conditions, but <B>23</B> rearranges under alkaline conditions to give, among other unidentified products, <I>N</I>-methyl-<I>N</I>-[<I>o</I>-(methylamino)phenyl]benzamide and 5,10-dihydro-5,10-dimethyl-2-phenazinecarbaldehyde. Reactions of title compounds with alkali and hydrogen peroxide are compared with those of <I>O</I>- and <I>S</I>-analogues.
- 公益社団法人 日本化学会の論文
著者
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Shindo Kimio
Department Of Chemistry Faculty Of Science Josai University
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Ishikawa Sumio
Departmant of Civil and Environmental Engineering, Yamanashi University
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Nozoe Tetsuo
Tokyo Reseach Laboratory of Kao Soap Co., Ltd.
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