The Nucleophilic Displacement Reactions of 8-Chloro- and 2,8-Dichloro-3-phenyl-1-azaazulenes
The Nucleophilic Displacement Reactions of 8-Chloro- and 2,8-Dichloro-3-phenyl-1-azaazulenes
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8-氯-和2,8-二氯-3-苯基-1-氮杂薁烯的亲核置换反应
DOI：
10.1246/bcsj.50.1184
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发表时间：
1977
期刊：
影响因子：
--
通讯作者：
T. Nozoe
中科院分区：
文献类型：
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作者：
K. Yamane;K. Fujimori;Je;T. Nozoe
3-苯基吡咯并[2,3-b]托酮(7)与磷酰氯反应得到8-氯-3-苯基-1-氮杂薁(5)。当5和7用N-氯代琥珀酰亚胺处理时，分别得到2,8-二氯-3-苯基-1-氮杂薁(6)和2-氯-3-苯基吡咯并[2,3-b]托品酮(8)。 6也是通过用磷酰氯处理由8得到的。 5和6与亲核试剂反应得到相应的取代产物（14a-m和15a-m）。将5和6与水合肼反应得到的8-肼基-3-苯基-1-氮杂薁(14m)和2-氯-8-肼基-3-苯基-1-氮杂薁(10)通过用硫酸铜(II)在乙酸中处理而分解，得到3-苯基-1-氮杂薁(2)和分别为2-氯-3-苯基-1-氮杂薁(11)。
The reaction of 3-phenylpyrrolo[2,3-b]tropone (7) with phosphoryl chloride gave 8-chloro-3-phenyl-1-azaazulene (5). When 5 and 7 were treated with N-chlorosuccinimide, 2,8-dichloro-3-phenyl-1-azaazulene (6) and 2-chloro-3-phenylpyrrolo[2,3-b]tropone (8) were obtained respectively. 6 was also obtained from 8 by treatment with phosphoryl chloride. The reactions of 5 and 6 with nucleophilic reagents gave the corresponding substituted products (14a–m and 15a–m). 8-Hydrazino-3-phenyl-1-azaazulene (14m) and 2-chloro-8-hydrazino-3-phenyl-1-azaazulene (10), which had been obtained by the reaction of 5 and 6 with hydrazine hydrate, were decomposed by treatment with copper(II) sulfate in acetic acid to give 3-phenyl-1 -azaazulene (2) and 2-chloro-3-phenyl-1-azaazulene (11) respectively.