Chinese Journal of Organic Chemistry >
Sequential Three-Component Reactions for the Assembly of Functionalized Pyrazoles
Received date: 2015-09-18
Revised date: 2015-11-12
Online published: 2015-12-07
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.
Key words： hydrazine; aldehyde; methyl propiolate; pyrazoles; three-component reaction
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
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