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Calcium carbide as the acetylide source: transition-metal-free synthesis of substituted pyrazoles via [1,5]-sigmatropic rearrangements†
Yue Yu,Wei Huang,Yang Chen,Bingjie Gao,Wanqing Wu,Huanfeng Jiang
Green Chemistry Pub Date : 10/28/2016 00:00:00 , DOI:10.1039/C6GC02776H
Abstract

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 regioselectivities. The transformations go through [3 + 2] cycloadditions followed by [1,5]-sigmatropic rearrangements, which are supported by deuterium-labeling experiments.

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