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N-加成

JOURNAL OF ORGANIC CHEMISTRY · 2019 · IF 4.745

Regioselective N-Addition/Substitution Reaction of α-Alkylidene Pyrazolinones with Propargyl Sulfonium Salts to Construct Allylthio-Containing Pyrazolones

Shou-Jie Shen,Xiao-Li Du,Xiao-Li Xu,Ming-Gang Zhao,Jin-Yan Liang

The regioselective N-addition/substitution reaction between α-alkylidene pyrazolinones and propargyl sulfonium salts has been developed to construct functionalized allylthio-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones act as N-nucleophilic agents which are distinguished from reported C-nucleophilic reactions. Excellent regioselectivity, readily available starting materials, the broad range of substrates, gram-scale synthesis, and simple operation illustrate the synthetic advantages of this new reaction pathway.

CAS / MDL: 112926-00-8

研究领域: 有机化学 · 合成化学 · 杂环化学

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RSC Advances · 2019 ·Vol. 9 ·期 60 ·34912-34925 · IF 3.049

Combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement to construct homoallyl sulfur-containing pyrazolones

Shou-Jie Shen,Xiao-Li Du,Xiao-Li Xu,Yue-Hua Wu,Ming-gang Zhao,Jin-Yan Liang

The first sequentially combined inorganic base promoted N-addition/[2,3]-sigmatropic rearrangement reaction of α-alkylidene pyrazolinones and propargyl sulfonium salts has been reported to construct homoallyl sulfur-containing pyrazolones with moderate to excellent yields. α-Alkylidene pyrazolinones function as N-nucleophilic agents distinguished from the reported C-addition reactions. Propargyl sulfonium salts were first involved in the [2,3]-sigmatropic rearrangement protocol differentiated from the well-established annulation reactions. The excellent regioselectivity, the broad scope of substrates, gram-scale synthesis and convenient transformation embody the synthetic superiority of this cascade process.

CAS / MDL: 112926-00-8

研究领域: 有机化学 · 合成化学

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