Calcium carbide as the acetylide source: transition-metal-free synthesis of substituted pyrazoles via [1,5]-sigmatropic rearrangements

被引：66

作者：

Yu, Yue ^{[1
]}

Huang, Wei ^{[1
]}

Chen, Yang ^{[1
]}

Gao, Bingjie ^{[1
]}

Wu, Wanqing ^{[1
]}

Jiang, Huanfeng ^{[1
]}

机构：

[1] South China Univ Technol, Sch Chem & Chem Engn, Key Lab Funct Mol Engn Guangdong Prov, Guangzhou 510640, Guangdong, Peoples R China

来源：

GREEN CHEMISTRY | 2016年 / 18卷 / 24期

基金：

中国国家自然科学基金;

关键词：

ONE-POT SYNTHESIS; N BOND-FORMATION; ORGANIC-SYNTHESIS; 3,5-DISUBSTITUTED PYRAZOLES; SIGMATROPIC REARRANGEMENT; TETRANYCHUS-URTICAE; CARBONYL-COMPOUNDS; TOSYLHYDRAZONES; KETONES; CASCADE;

D O I：

10.1039/c6gc02776h

中图分类号：

O6 [化学];

学科分类号：

0703 ;

摘要：

Under transition-metal-free conditions, calcium carbide was used as the acetylide source to react with a wide range of N-tosylhydrazones derived from aldehydes or ketones, affording various substituted pyrazoles in good yields with high regio-selectivities. The transformations go through [3 + 2] cycloadditions followed by [1,5]-sigmatropic rearrangements, which are supported by deuterium-labeling experiments.

引用

页码：6445 / 6449

页数：5

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