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肟基结构化合物成环反应的研究

STUDY ON THE REACTION OF FORMING CYCLE FROM OXIMIDO COMPOUNDS

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【作者】 刘焕梅; 耿谦; 张育兵; 吴连春;

【Author】 Liu Huanmei, Geng Qian, Zhang Yubing and Wu Lianchun (Institute of Light Industry , Hebei Polytechnic University , Tangshan 063020, Hebei, China)

【机构】 河北理工大学轻工学院; 河北理工大学轻工学院 河北唐山063020; 河北唐山063020;

【摘要】 在氢氧化钾-二甲亚砜(KOH-DMSO)催化体系中,肟基结构化合物与乙炔发生成环反应,生成含有吡咯环结构的化合物。研究了4-(5’-甲基-2’-噻吩基)-2-丁酮肟与乙炔作用,形成同时含有噻吩环和吡咯环的杂环化合物:2-甲基-3-(5’-甲基-2’-噻吩基)甲基吡咯及1-乙烯基-2-甲基-3-(5’-甲基-2’-噻吩基)甲基吡咯,其最佳反应条件为:前者为常压、95℃,收率为48.2%;后者为压力1.5 MPa、100℃,收率为34.5%。催化剂以25 mL DMSO中加0.8 g KOH为宜。产物IR及1H NMR均与文献值一致。

【Abstract】 Pyridine-ring containing compounds were synthesized from oximido compounds and acetylene catalyzed by KOH-DMSO. The reaction of 4-(5’-methyl-2’-thiophenyl)-2-butanone oxime with a-cetylene was specifically studied for the synthesis of heterocyclic compound containing both thiophene-cycle and pyridine-cycle, e. g. , 2-metyl-3-(5’-methyl-2’-thiophenyl)-methylpyrrole and 1-vinyl-2-methyl-3-(5’-methyl-2’-thiophenyl)-methyl pyridine. The optimal conditions for former product were: normal pressure and 95℃, with the yield of 48. 2%; while those for the later product were 1. 5 MPa and 100℃, with the yield of 34. 5%. The optimal catalyst for both the products was the same,i. e. , KOH : DMSO/(g : mL) = 0. 8 : 25. Results of IR and 1H NMR of the products agreed well with those in the literature.

【关键词】 肟基结构化合物; 乙炔; 成环反应;
【Key words】 oximido compounds; acetylene; cyclization;
  • 【文献出处】 精细石油化工 ,Speciality Petrochemicals , 编辑部邮箱 ,2006年05期
  • 【分类号】O621.25
  • 【下载频次】165
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