Three-component synthesis of C(2)F(5)-substituted pyrazoles from C(2)F(5)CH(2)NH(2)·HCl, NaNO(2) and electron-deficient alkynes

A one-pot reaction between C(2)F(5)CH(2)NH(2)·HCl, NaNO(2) and electron-deficient alkynes gives C(2)F(5)-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 chromat...

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Detalles Bibliográficos
Autor principal: Mykhailiuk, Pavel K
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4311722/
https://www.ncbi.nlm.nih.gov/pubmed/25670987
http://dx.doi.org/10.3762/bjoc.11.3
Descripción
Sumario:A one-pot reaction between C(2)F(5)CH(2)NH(2)·HCl, NaNO(2) and electron-deficient alkynes gives C(2)F(5)-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, C(2)F(5)CH(2)NH(2)·HCl and NaNO(2) react first in water to generate C(2)F(5)CHN(2), that participates in a [3 + 2] cycloaddition with electron-deficient alkynes in dichloromethane.

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