Chinese Journal of Organic Chemistry ›› 2021, Vol. 41 ›› Issue (8): 3256-3263.DOI: 10.6023/cjoc202103008 Previous Articles     Next Articles



徐长明*(), 黄金程   

  1. 兰州交通大学化学化工学院 兰州 730070
  • 收稿日期:2021-03-04 修回日期:2021-04-06 发布日期:2021-05-08
  • 通讯作者: 徐长明
  • 基金资助:
    国家自然科学基金(21662024); 国家自然科学基金(22061025); 甘肃省自然科学基金(20JR10RA220); 兰州交通大学百名青年人才培训计划资助项目

Highly Efficient Synthesis of 1H-Indazole-3-carboxylic Acid Derivatives via Diazotization Reaction

Changming Xu(), Jincheng Huang   

  1. School of Chemistry and Chemical Engineering, Lanzhou Jiaotong University, Lanzhou 730070
  • Received:2021-03-04 Revised:2021-04-06 Published:2021-05-08
  • Contact: Changming Xu
  • Supported by:
    National Natural Science Foundation of China(21662024); National Natural Science Foundation of China(22061025); Natural Science Foundation of Gansu Province(20JR10RA220); Foundation of a Hundred Youth Talents Training Program of Lanzhou Jiaotong University

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