Chinese Journal of Organic Chemistry >
Highly Efficient Synthesis of 1H-Indazole-3-carboxylic Acid Derivatives via Diazotization Reaction
Received date: 2021-03-04
Revised date: 2021-04-06
Online published: 2021-05-08
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.
Changming Xu , Jincheng Huang . Highly Efficient Synthesis of 1H-Indazole-3-carboxylic Acid Derivatives via Diazotization Reaction[J]. Chinese Journal of Organic Chemistry, 2021 , 41(8) : 3256 -3263 . DOI: 10.6023/cjoc202103008
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