摘要/Abstract

报道了邻氨基苯乙酰胺和邻氨基苯乙酸酯在重氮化试剂作用下直接转化为对应的1H-吲唑-3-羧酸衍生物. 该反应操作简单, 反应条件温和, 反应迅速, 产率高, 底物范围广, 为1H-吲唑-3-羧酸衍生物的合成提供了一种更加高效简洁的新方法. 该方法被成功应用于药物分子格拉司琼和氯尼达明的合成, 分别以46%和60%的总收率得到了目标产物. 初步的机理研究表明重氮盐是该反应的关键中间体.
关键词: 1H-吲唑-3-羧酸衍生物, 重氮化, 格拉司琼, 氯尼达明
Direct conversion of ortho-aminobenzacetamides and ortho-aminobenzacetates to the corresponding 1H-indazole- 3-carboxylic acid derivatives under the action of diazotization reagents was reported. This method features operational simplicity, mild reaction conditions, rapid reaction rates, high yields, wide substrate scope, offering an efficient and concise route to synthesis of 1H-indazole-3-carboxylic acid derivatives. The drugs granisetron and lonidamine were synthesized successfully using this protocol with 46% and 60% total yields, respectively. Preliminary mechanistic study suggests that diazonium salt is a key intermediate.
Key words: 1H-indazole-3-carboxylic acid derivatives, diazotization, granisetron, lonidamine


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