三氮唑螺氧化吲哚衍生物的合成及表征  

Synthesis and Characterization of Spirotriazoline Oxindoles Derivatives

作　　者：王龙 张文静 曹国锐[1] WANG Long;ZHANG Wen-jing;CAO Guo-rui(College of Chemistry Engineering,Qingdao University of Science and Technology,Qingdao 266042,China)

机构地区：[1]青岛科技大学化工学院,山东青岛266042

出　　处：《化学试剂》2021年第4期546-553,共8页Chemical Reagents

摘　　要：以1-苄基-2-氧代吲哚-3-亚氨基甲酸叔丁脂和4-取代(Z)-N-苯基苯甲酰氯为底物通过1,3-偶极环加成反应合成了9种目标产物。通过比较目标产物的产率,对反应溶剂、碱及其用量、温度等因素进行了优化,确定了最佳反应条件,即在25℃下以二氯甲烷为溶剂、三乙胺为碱,且n(Et3N)∶n(1-苄基-2-氧代吲哚-3-亚氨基甲酸叔丁脂)=2.0∶1.0时,目标化合物最高产率可达94.4%。将具有生物活性的三氮唑骨架引入到螺环氧化吲哚骨架中,为更好地发现具有生物活性的该类新化合物提供借鉴。1-Benzyl-2-oxoindole-3-iminocarboxylic acid tert-butyl ester and 4-substituted(Z)-N-phenylbenzoyl chloride were used as substrates through 1,3-dipolar cycloaddition reaction to give nine spirotriazoline oxindoles compounds.The following 1,3-dipolar cycloaddition reaction was studied by exploring reaction solvent, base and its equivalent and temperature to found the optimized reaction conditions.The dichloromethane as the solvent and triethylamine as the base at 25 ℃,and n(Et3N)∶n(1-benzyl-2-oxoindole-3-iminocarboxylic acid tert-butyl ester)=2.0∶1.0,the highest yield of the target product was 94.4%.The triazole skeleton with biological activity is successfully introduced into the spiroepoxy indole skeleton, which provides a reference for better discovering such new compounds with biological activity.

关 键 词：1-苄基-2-氧代吲哚-3-亚氨基甲酸叔丁脂 4-取代(Z)-N-苯基苯甲酰氯 1 3-偶极环加成反应 三氮唑螺氧化吲哚化合物 

分 类 号：O626.13[理学—有机化学]