Citation: Li Yufeng, Huang Jiawei, Gu Jiachao, Huang Hao, Niu Changsheng, Ma Hongfei. Sequential Three-Component Reactions for the Assembly of Functionalized Pyrazoles[J]. Chinese Journal of Organic Chemistry, ;2016, 36(3): 520-526. doi: 10.6023/cjoc201509020 shu

Sequential Three-Component Reactions for the Assembly of Functionalized Pyrazoles

1.
College of Chemistry and Molecular Engineering, Nanjing Tech University, Nanjing 211816

Corresponding author: Li Yufeng,
Received Date: 18 September 2015
Available Online: 12 November 2015

A sequential three-component reaction for the assembly of functionalized pyrazoles is described. Aldehydes are treated with hydrazines in dichloroethane to generate hydrazones (3), which in situ take place aza-Michael reaction quickly with methyl propiolate (4) catalyzed by CuCl to give Michael adducts (5). Subsequent oxidation of 5 with stoichiometric FeCl₃ provides substituted pyrazoles with high to excellent yields. The intermediates of the synthetic method are not necessary to isolate. Aliphatic hydrazines, aromatic hydrazines as well as aromatic aldehydes are well adaptable to the reaction.
- hydrazine,
- aldehyde,
- methyl propiolate,
- pyrazoles,
- three-component reaction
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