The nucleophilic displacement reactions of 8-chloro- and 2,8-dichloro-3-phenyl-1-azaazulenes.

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概要

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• The reaction of 3-phenylpyrrolo[2,3-<I>b</I>]tropone (<B>7</B>) with phosphoryl chloride gave 8-chloro-3-phenyl-1-azaazulene (<B>5</B>). When <B>5</B> and <B>7</B> were treated with <I>N</I>-chlorosuccinimide, 2,8-dichloro-3-phenyl-1-azaazulene (<B>6</B>) and 2-chloro-3-phenylpyrrolo[2,3-<I>b</I>]tropone (<B>8</B>) were obtained respectively. <B>6</B> was also obtained from <B>8</B> by treatment with phosphoryl chloride. The reactions of <B>5</B> and <B>6</B> with nucleophilic reagents gave the corresponding substituted products (<B>14a</B>–<B>m</B> and <B>15a</B>–<B>m</B>). 8-Hydrazino-3-phenyl-1-azaazulene (<B>14m</B>) and 2-chloro-8-hydrazino-3-phenyl-1-azaazulene (<B>10</B>), which had been obtained by the reaction of <B>5</B> and <B>6</B> with hydrazine hydrate, were decomposed by treatment with copper(II) sulfate in acetic acid to give 3-phenyl-1 -azaazulene (<B>2</B>) and 2-chloro-3-phenyl-1-azaazulene (<B>11</B>) respectively.

• 公益社団法人 日本化学会の論文

著者

• Fujimori Kunihide

  Department Of Chemistry Faculty Of Science Shinshu University

• Nozoe Tetsuo

  Department of Chemistry Faculty of Science Tohoku University

• Yamane Kameji

  Department of Chemistry, Faculty of Science, Shinshu University

• Sin Je-Kyun

  Department of Chemistry, Faculty of Science, Tohoku University

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• The Synthesis of 1-Phenylazulene and 2-Phenylazulene from the Troponoid Compound
• The Synthesis of 7-Isopropyl-2,4-dimethylazulene (Se-Guaiazulene) from 4-Isopropyltropolone

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