Synthesis and some reactions of 2-(2-aminoanilino)cyclohepta(b)pyrroles: Leading to 5H-cyclohepta(1', 2': 4, 5)pyrrolo(2,3-b)(1, 5)benzodiazepine, a novel 20.PI. antiaromatic system, and cyclohepta(1', 2': 4, 5)-pyrrolo(1,2-a)benzimidazoles.
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概要
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2-Chlorocyclohepta[<I>b</I>]pyrroles reacted with <I>o</I>-phenylenediamine to give 2-(2-aminoanilino)cyclohepta[<I>b</I>]pyrroles (<B>2a</B>,<B>b</B>) in good yields. Treatment of <B>2a</B> and <B>2b</B> with polyphosphoric acid afforded cyclohepta[1′,2′: 4,5]pyrrolo[1,2-<I>a</I>]benzimidazole (<B>4a</B>) in good yields. Treatment of <B>2b</B> with acids gave 6-(ethoxycarbonyl) derivatives (<B>4b</B>) of <B>4a</B> and 12<I>H</I>-5,13-dihydrocyclohepta[1′,2′: 4,5]pyrrolo[2,3-<I>b</I>][1,5]benzodiazepin-12-one (<B>5</B>). Compound 5 was methylated with methyl iodide in the presence of DBU to give 5<I>H</I>-12-methoxycyclohepta[1′,2′: 4,5]pyrrolo[2,3-<I>b</I>][1,5]benzodiazepine, a novel 20π antiaromatic system. Treatment of <B>2b</B> with sodium ethoxide gave <B>4b</B> and 2<I>H</I>-1-(cyclohepta[<I>b</I>]pyrrol-2-yl)-1,3-dihydrobenzimidazol-2-one (<B>7a</B>). Compound <B>5</B> rearranged to <B>7a</B> in the refluxing sodium ethoxide-ethanol solution. Reactions of <B>2a</B> and <B>2b</B> with triethyl orthoformate gave corresponding 1-(cyclohepta[<I>b</I>]pyrrol-2-yl)benzimidazoles. Reactions of <B>2a</B> and <B>2b</B> with acetic anhydride are also mentioned.
- 公益社団法人 日本化学会の論文
著者
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Miura Yoshiaki
Department Of Biochemistry Chiba University School Of Medicine
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Hayashi Takashi
Department Of Applied Chemistry Graduate School Of Engineering Osaka University
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Abe Noritaka
Department Of Pure And Applied Chemistry Faculty Of Science And Technology Tokyo University Of Scien
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Miura Yoshiaki
Department of Chemistry, Faculty of Science, Yamaguchi University
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Ishikawa Naomi
Department of Chemistry, Faculty of Science, Yamaguchi University
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