河北师范大学学报—

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
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一锅三组分串联反应合成-2,3-二酯基-2,4-二苯基-1,5-苯并二氮杂䓬化合物

安晓英¹

白帆¹

李文红²

王兰芝¹

1. 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;
2. 河北工业职业技术学院环境与化学工程系, 河北石家庄 050091
DOI： 10.13763/j.cnki.jhebnu.nse.202103004

Synthesis of 2,3-diester-2,4-diphenyl-1,5-benzodiazepines Compounds via One-pot Three-component Tandem Reactions

AN Xiaoying¹, BAI Fan¹, LI Wenhong², WANG Lanzhi¹

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摘要/Abstract

摘要：

以取代的邻苯二胺、苯甲酰乙酸乙酯、苯甲酰甲酸乙酯为原料，无水乙醇为溶剂，对甲苯磺酸为催化剂，一锅三组分串联反应成功合成了7种新的亚胺结构的2，3-二酯基-2，4-二苯基-1，5-苯并二氮杂䓬化合物. 该串联反应历经2次亲核加成-脱水反应过程，形成分子内含有亚胺和烯胺结构的活性中间体，再经分子内的碳碳偶联环合和质子迁移形成目标化合物. 针对该三组分串联反应提出了合理的反应机理. 该合成方法具有环境友好、反应条件温和、底物范围广等优点，为苯并七元含氮杂环化合物提供绿色环保、高效简便的合成思路.

Abstract：

In this paper, seven novel 2,3-diester-2,4-diphenyl-1,5-benzodiazepines with imine structure were obtained via one-pot three-component tandem reactions catalyzed by TsOH in ethanol. With substituted 1,2-phenylenediamines, ethyl benzoylacetate and ethyl benzoylformate as the raw materials,the tandem reactions undergo two nucleophilic addition-dehydration processes to form the active intermediate molecules containing imine and enamine structures, further undergo carbon-carbon coupling cyclization and hydrogen transfer to yield the target products. A reasonable reaction mechanism is proposed for this three-component tandem reaction. The synthesis has the advantages of environliness, mild reaction conditions, wide substrate range, etc, which provides a green, efficient and convenient synthetic route for nitrogen-containing heterocyclic compounds.

关键词

关键词： 一锅法 ; 串联反应 ; 亚胺结构 ; 1,5-苯并二氮杂䓬

Key words： one-pot ; tandem reaction ; imine structure ; 1,5-benzodiazepines

参考文献 7

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