Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2•HCl, NaNO2 and electron-deficient alkynes

被引：36

作者：

Mykhailiuk, Pavel K. ^{[1
,2
]}

机构：

[1] Enamine Ltd, UA-01103 Kiev, Ukraine

[2] Taras Shevchenko Natl Univ Kyiv, Dept Chem, UA-01601 Kiev, Ukraine

来源：

BEILSTEIN JOURNAL OF ORGANIC CHEMISTRY | 2015年 / 11卷

关键词：

cycloaddition; fluorine; pentafluoroethyl group; pentafluoroethyldiazomethane; pyrazole; NONNUCLEOSIDE INHIBITORS; MEDICINAL CHEMISTRY; BIOLOGICAL-ACTIVITY; CHANNEL INHIBITORS; IN-SITU; POTENT; FLUORINE; PHARMACEUTICALS; CYCLOADDITION;

D O I：

10.3762/bjoc.11.3

中图分类号：

O62 [有机化学];

学科分类号：

070303 ; 081704 ;

摘要：

A one-pot reaction between C2F5CH2NH2 center dot HCl, NaNO2 and electron-deficient alkynes gives C2F5-substituted pyrazoles in excellent yields. The transformation smoothly proceeds in dichloromethane/water, tolerates the presence of air, and requires no purification of products by column chromatography. Mechanistically, C2F5CH2NH2 center dot HCl and NaNO2 react first in water to generate C2F5CHN2, that participates in a [3 + 2] cycloaddition with electron-deficient alkynes in dichloromethane.

引用

页码：16 / 24

页数：9

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