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取代1-吲酮的α-溴代反应

α-Bromination Reaction of Substituted 1-Indanones

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【作者】 张睿徐云根华维一

【Author】 ZHANG Rui,XU Yun-gen,HUA Wei-yi(Center of Drug Discovery,China Pharmaceutical University,Nanjing 210009,China)

【机构】 中国药科大学新药研究中心中国药科大学新药研究中心 江苏南京210009江苏南京210009

【摘要】 从取代3-苯丙酸出发,在多聚磷酸中直接环合(或先生成酰氯,再以三氯化铝催化环合)得到12个取代1-吲酮(Ⅰa~Ⅰl)。Ⅰ10 mmol溶于40 mL混合溶剂[V(乙酸乙酯)∶V(氯仿)=1∶1]中,搅拌下回流,分3批加入溴化铜(60%,24%和16%),经α-溴代反应得取代2-溴-1-吲酮(Ⅱa~Ⅱl,其中Ⅱf,Ⅱj,Ⅱk和Ⅱl未见文献报道),收率67.2%~91.5%。新化合物的结构经1H NMR确证。

【Abstract】 Twelve substituted 1-indanones(Ⅰa~Ⅰl) were prepared either by the cyclization reaction of substituted 3-phenylpropanoic acid in the presence of polyphosphoric acid,or from the corresponding acid chloride in the presence of aluminum chloride.2-bromo-1-indanones(Ⅱa~Ⅱl,Ⅱf,Ⅱj,(Ⅱk) and Ⅱl were novel compounds) in yields of 67.2%~91.5% were synthesized by the bromination reaction of Ⅰ using copper(Ⅱ) bromide as a bromination regent.The reaction conditions were as follows: Ⅰ 10 mmol was dissolved in 20 mL ethyl acetate and 20 mL chloroform,copper(Ⅱ) bromide was added by three times(60%,24% and 16% each) under reflux.The structures of the novel compounds were confirmed by ~1H NMR.

  • 【文献出处】 合成化学 ,Chinese Journal of Synthetic Chemistry , 编辑部邮箱 ,2006年05期
  • 【分类号】O621.25
  • 【被引频次】2
  • 【下载频次】406
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