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三氯异氰尿酸促进β,γ-不饱和腙的串联环化/三氟甲基化合成三氟乙基吡唑啉。

Synthesis of Trifluoroethyl Pyrazolines via Trichloroisocyanuric Acid Promoted Cascade Cyclization/Trifluoromethylation of β,γ-Unsaturated Hydrazones.

机构信息

College of Chemistry and Chemical Engineering , Northwest Normal University , 967 Anning East Road , Lanzhou 730070 , China.

State Key Laboratory of Applied Organic Chemistry , Lanzhou University , Lanzhou 730000 , China.

出版信息

J Org Chem. 2018 Apr 20;83(8):4365-4374. doi: 10.1021/acs.joc.8b00009. Epub 2018 Apr 3.

Abstract

A novel and efficient protocol for the construction of trifluoroethyl pyrazolines has been developed by cascade cyclization/trifluoromethylation reaction of β,γ-unsaturated hydrazones. This strategy uses cheap and commercially available trichloroisocyanuric acid as promoter and TMSCF as the trifluoromethylating reagent, which make the trifluoromethylating process much cheaper. A wide range of substrates can be applied in this process to afford the trifluoroethyl pyrazolines in good yield.

摘要

一种新型、高效的三氟乙基吡唑啉类化合物的合成方法,通过β,γ-不饱和腙的级联环化/三氟甲基化反应实现。该策略使用廉价且市售的三氯异氰尿酸作为促进剂,TMSCF 作为三氟甲基化试剂,使三氟甲基化过程更加经济实惠。该方法适用于多种底物,以较高的产率得到三氟乙基吡唑啉类化合物。

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