Regio- and Stereoselective Switchable Synthesis of (E)- and (Z)-N-Carbonylvinylated Pyrazoles

被引：2

作者：

Zhang, Xue ^{[1
]}

Zhang, Zheyu ^{[1
]}

Yu, Haifeng ^{[1
]}

Che, Guangbo ^{[1
]}

机构：

[1] Baicheng Normal Univ, Coll Chem, Baicheng 137000, Peoples R China

来源：

MOLECULES | 2023年 / 28卷 / 11期

关键词：

silver carbonate; Michael addition; pyrazoles; alkynes; stereoselectivity; VINYLATION REACTIONS; COPPER; DISCOVERY; ARYLATION; AZOLES; POTENT; CHEMO;

D O I：

10.3390/molecules28114347

中图分类号：

Q5 [生物化学]; Q7 [分子生物学];

学科分类号：

071010 ; 081704 ;

摘要：

Regio- and stereoselective switchable synthesis of (E)- and (Z)-N-carbonylvinylated pyrazoles is first developed by using the Michael addition reaction of pyrazoles and conjugated carbonyl alkynes. Ag2CO3 plays a key role in the switchable synthesis of (E)- and (Z)-N-carbonylvinylated pyrazoles. Ag2CO3-free reactions lead to thermodynamically stable (E)-N-carbonylvinylated pyrazoles in excellent yields whereas reactions with Ag2CO3 give (Z)-N-carbonylvinylated pyrazoles in good yields. It is noteworthy that (E)- or (Z)-N-1-carbonylvinylated pyrazoles are obtained with high regioselectivity when asymmetrically substituted pyrazoles react with conjugated carbonyl alkynes. The method can also extend to the gram scale. A plausible mechanism is proposed on the basis of the detailed studies, wherein Ag+ acts as coordination guidance.

引用

页数：10

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