串联式三组分反应构建取代吡唑杂环
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
李玉峰 , 黄佳维 , 顾嘉超 , 黄浩 , 钮长盛 , 马鸿飞 . 串联式三组分反应构建取代吡唑杂环[J]. 有机化学, 2016 , 36(3) : 520 -526 . DOI: 10.6023/cjoc201509020
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
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