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串联反应一锅合成茚酮稠合1,5-苯并二氮杂■化合物

One-pot Synthesis of Indanone Fused 1,5-benzodiazepines by Tandem Reaction

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【作者】 茹慧慧白帆王兰芝

【Author】 RU Huihui;BAI Fan;WANG Lanzhi;College of Chemistry and Materials Science, Hebei Normal University,Hebei Key Laboratory of Organic Functional Molecules;

【通讯作者】 王兰芝;

【机构】 河北师范大学化学与材料科学学院,河北省有机功能分子重点实验室

【摘要】 以取代的邻苯二胺、1,3-茚满二酮、醛类化合物(苯乙醛,苯丙醛)为原料,无水乙醇为溶剂,对甲苯磺酸为催化剂,应用串联反应一锅合成了8种结构新颖的茚酮稠合1,5-苯并二氮杂■化合物.该串联反应经历了两次亲核加成-消除反应过程,形成含烯胺和亚胺结构的活性中间体,再经分子内碳碳偶联环合和质子迁移形成了目标化合物,针对该三组分串联反应提出了合理的反应机制.该方法具有新颖、绿色环保、反应条件温和、底物范围广等诸多优点,为苯并二氮杂■化合物的合成提供了高效简便的新思路.

【Abstract】 Eight novel indanone fused 1,5-benzodiazepine compounds were synthesized by one-pot tandem reaction using substituted o-phenylenediamine, 1,3-indandione, and aldehydes(phenylacetaldehyde, phenylpropanal) as raw materials, absolute ethanol as solvent and p-toluenesulfonic acid as catalyst.Experiments showed that the tandem reaction underwent two nucleophilic addition-elimination reaction processes to form an active intermediate containing both enamine and imine structures, and then the target compound was formed through intramolecular carbon-carbon coupling cyclization and proton transfer.A reasonable reaction mechanism was provided for the three-component tandem reaction.The synthesis method has many advantages, such as novelty, green environmental protection, mild reaction conditions, wide range of substrates, which provides a new efficient and convenient approach for the synthesis of benzodiazepine compounds.

【基金】 国家自然科学基金(21776060)
  • 【文献出处】 河北师范大学学报(自然科学版) ,Journal of Hebei Normal University(Natural Science) , 编辑部邮箱 ,2024年02期
  • 【分类号】O626
  • 【下载频次】38
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