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C2F5CH2NH2·HCl、NaNO2 和缺电子炔烃三组分合成 C2F5 取代吡唑。

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

机构信息

Enamine Ltd., Vul. Oleksandra Matrosova 23, 01103 Kyiv, Ukraine; and Department of Chemistry, Taras Shevchenko National University of Kyiv, Volodymyrska Street, 64, Kyiv 01601, Ukraine.

出版信息

Beilstein J Org Chem. 2015 Jan 6;11:16-24. doi: 10.3762/bjoc.11.3. eCollection 2015.

DOI:10.3762/bjoc.11.3
PMID:25670987
原文链接:https://pmc.ncbi.nlm.nih.gov/articles/PMC4311722/
Abstract

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.

摘要

一釜反应将 C2F5CH2NH2·HCl、NaNO2 和缺电子炔烃反应生成 C2F5 取代的吡唑，产率极好。该转化在二氯甲烷/水体系中顺利进行，耐受空气存在，且产物无需通过柱色谱纯化。从机理上看，C2F5CH2NH2·HCl 和 NaNO2 首先在水中反应生成 C2F5CHN2，后者在二氯甲烷中与缺电子炔烃发生[3+2]环加成反应。

https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/c30cd92d8cb8/Beilstein_J_Org_Chem-11-16-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/07f744ce5cca/Beilstein_J_Org_Chem-11-16-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/a453f73afdbf/Beilstein_J_Org_Chem-11-16-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/83f5f717723d/Beilstein_J_Org_Chem-11-16-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/f96259a12b94/Beilstein_J_Org_Chem-11-16-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/e6c8b577a73f/Beilstein_J_Org_Chem-11-16-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/433c3b84af31/Beilstein_J_Org_Chem-11-16-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/c30cd92d8cb8/Beilstein_J_Org_Chem-11-16-g008.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/07f744ce5cca/Beilstein_J_Org_Chem-11-16-g002.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/a453f73afdbf/Beilstein_J_Org_Chem-11-16-g003.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/83f5f717723d/Beilstein_J_Org_Chem-11-16-g004.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/f96259a12b94/Beilstein_J_Org_Chem-11-16-g005.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/e6c8b577a73f/Beilstein_J_Org_Chem-11-16-g006.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/433c3b84af31/Beilstein_J_Org_Chem-11-16-g007.jpg
https://cdn.ncbi.nlm.nih.gov/pmc/blobs/1975/4311722/c30cd92d8cb8/Beilstein_J_Org_Chem-11-16-g008.jpg

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