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Ag 2 O-Induced Regioselective Huisgen Cycloaddition for the Synthesis of Fully Substituted Pyrazoles as Potential Anticancer Agents.

Qianqian XuJifan JiaYuqing WuBo HuJiaqi XinYi LiuWei GaoDan Li
Published in: The Journal of organic chemistry (2022)
Efficient regioselective synthesis of novel fully substituted pyrazoles has been achieved through Huisgen cycloaddition reaction of δ-acetoxy allenoates with hydrazonoyl chlorides by the addition of Ag 2 O. The present approach offers the advantages of simpleness, high efficiency, mild conditions, wide substrate scope, and good-to-excellent regioselectivities. The strategy could be performed on a large-scale pattern to allow access to structurally versatile pyrazoles, of which a key intermediate of lonazolac (303), a nonsteroidal anti-inflammatory drug, could be synthesized efficiently. Moreover, several pyrazoles show obvious growth-inhibitory activity of Huh-7 cells, expected as potential anticancer agents.
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