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

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

A one-pot reaction between C2F5CH2NH2·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. Mecha...

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Main Author: Pavel K. Mykhailiuk
Format: Article
Language:English
Published: Beilstein-Institut 2015-01-01
Series:Beilstein Journal of Organic Chemistry
Subjects:
cycloaddition
fluorine
pentafluoroethyl group
pentafluoroethyldiazomethane
pyrazole
Online Access:https://doi.org/10.3762/bjoc.11.3
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spelling doaj-94f236d2a77e4854bfa97626ef620bf12021-02-02T00:48:47ZengBeilstein-InstitutBeilstein Journal of Organic Chemistry1860-53972015-01-01111162410.3762/bjoc.11.31860-5397-11-3Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynesPavel K. Mykhailiuk0Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine; and Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street, 64, Kyiv 01601, UkraineA one-pot reaction between C2F5CH2NH2·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·HCl and NaNO2 react first in water to generate C2F5CHN2, that participates in a [3 + 2] cycloaddition with electron-deficient alkynes in dichloromethane.https://doi.org/10.3762/bjoc.11.3cycloadditionfluorinepentafluoroethyl grouppentafluoroethyldiazomethanepyrazole
collection DOAJ
language English
format Article
sources DOAJ
author Pavel K. Mykhailiuk
spellingShingle Pavel K. Mykhailiuk
Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes
Beilstein Journal of Organic Chemistry
cycloaddition
fluorine
pentafluoroethyl group
pentafluoroethyldiazomethane
pyrazole
author_facet Pavel K. Mykhailiuk
author_sort Pavel K. Mykhailiuk
title Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes
title_short Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes
title_full Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes
title_fullStr Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes
title_full_unstemmed Three-component synthesis of C2F5-substituted pyrazoles from C2F5CH2NH2·HCl, NaNO2 and electron-deficient alkynes
title_sort three-component synthesis of c2f5-substituted pyrazoles from c2f5ch2nh2·hcl, nano2 and electron-deficient alkynes
publisher Beilstein-Institut
series Beilstein Journal of Organic Chemistry
issn 1860-5397
publishDate 2015-01-01
description A one-pot reaction between C2F5CH2NH2·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·HCl and NaNO2 react first in water to generate C2F5CHN2, that participates in a [3 + 2] cycloaddition with electron-deficient alkynes in dichloromethane.
topic cycloaddition
fluorine
pentafluoroethyl group
pentafluoroethyldiazomethane
pyrazole
url https://doi.org/10.3762/bjoc.11.3
work_keys_str_mv AT pavelkmykhailiuk threecomponentsynthesisofc2f5substitutedpyrazolesfromc2f5ch2nh2hclnano2andelectrondeficientalkynes
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