期刊信息
- 刊名： 河北师范大学学报（自然科学版）Journal of Hebei Normal University (Natural Science)
- 主办： 河北师范大学
- ISSN： 1000-5854
- CN： 13-1061/N
- 中国科技核心期刊
- 中国期刊方阵入选期刊
- 中国高校优秀科技期刊
- 华北优秀期刊
- 河北省优秀科技期刊
串联反应合成苯基/甲基及乙氧羰基甲基取代的稠合1,5-苯并二氮杂䓬化合物
- 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，河北 石家庄 050024
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DOI：10.13763/j.cnki.jhebnu.nse.202503015
Synthesis of Phenyl/methyl and Ethoxy Carbonyl Methyl Substituted Fused 1,5-benzodiazepine Compounds via Tandem Reaction
摘要/Abstract
以(取代的)1,2-苯二胺、苯甲酰乙酸乙酯/乙酰乙酸乙酯、环状-1,3-二酮为原料，无水乙醇为溶剂，对甲基苯磺酸为催化剂，通过三组分串联一锅法成功合成了7种具有苯基/甲基及乙氧羰基甲基取代的稠合1,5-苯并二氮杂䓬化合物.该反应历经2次亲核加成-消除反应，形成了亚胺-烯胺/烯胺-烯胺中间体，再经分子内C—C偶联环合反应，最终生成2位苯基/甲基和乙氧羰基甲基取代3,4位环戊烯酮稠合的1,5-苯并二氮杂䓬化合物.该合成方法新颖高效、绿色经济且易于催化，所合成的目标化合物丰富了1,5-苯并二氮杂䓬化合物的结构多样性.
Seven fused 1,5-benzodiazepine compounds with phenyl/methyl and ethoxy carbonyl methyl substituents were successfully synthesized via three-component tandem one-pot reactions,using(substituted) 1,2-phenylenediamines,ethyl benzoylacetate/ethyl acetoacetate,and cyclic 1,3-diketones as starting materials,anhydrous ethanol as the solvent,and p-toluenesulfonic acid as the catalyst.The reactions proceeded through two nucleophilic addition-elimination reactions to form imide-enamine/enamine-enamine interme-diates,followed by an intramolecular C—C coupling cyclization reaction,ultimately yielding 1,5-benzodiaz-epine compounds fused with 2-position phenyl/methyl and ethoxy carbonyl methyl substituted 3,4-position cyclopentenones.The synthesis method is novel,environmentally benign,efficient,economical,and easily catalyzed.And the synthesized target compounds further enrich the structural diversity of 1,5-benzodiazepine compounds.
关键词
参考文献 19
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