综合有机化学实验:三唑并嘧啶类化合物的合成与表征

Comprehensive Organic Chemistry Experiment:Synthesis and Characterization of Triazolopyrimidine Compounds

以3-氨基-5-巯基-1,2,4-三氮唑、溴化苄和乙氧基亚甲基丙二酸二乙酯(EMME)为原料,经过亲核取代反应、缩合反应和水解反应,制备出含羧基及硫醚结构单元的三唑并嘧啶类化合物,并对产物进行结构表征分析。实验操作涉及加热回流、TLC(薄层层析色谱)检测、抽滤和重结晶等,有利于提高学生有机化合物多步合成及波谱解析能力。三唑嘧啶类化合物广泛存在于天然产物和药物中,学习该类化合物的合成不仅能通过实验内容了解社会需求,而且能结合前沿成果及课堂讲授的理论知识,提升实验内容的教学质量,取得良好的教学效果。

Triazolopyrimidine compounds containing carboxyl and thioether groups were synthesized using 3-amino-5-mercapto-1,2,4-triazole,benzyl bromide,and diethyl ethoxymethylenemalonate(EMME)as starting materials.The synthesis involved nucleophilic substitution,cyclization,and hydrolysis reactions.The resulting products were characterized and analyzed for their structures.The experiment included techniques such as heating reflux,TLC(thinlayer chromatography)detection,filtration,and recrystallization,which aimed to enhance students’skills in multi-step organic compound synthesis and spectral analysis.Triazolopyrimidine compounds are widely found in natural products and pharmaceuticals.The synthesis of these compounds not only provides insight into societal demands but also integrates cutting-edge research and theoretical knowledge taught in the classroom,thereby improving the quality of experimental teaching and achieving excellent educational outcomes.