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Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones

The Chan–Evans–Lam reaction of 1-unsubstituted 4-fluoroalkylpyrimidin-2(1Н)-ones with arylboronic acids is reported as a facile synthetic route to hitherto unavailable N1-(het)aryl and N1-alkenyl derivatives of the corresponding pyrimidines. An efficient C–N bond-forming process is also observed by...

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Autores principales: Tkachuk, Viktor M, Lukianov, Oleh O, Vovk, Mykhailo V, Gillaizeau, Isabelle, Sukach, Volodymyr A
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2020
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7509380/
https://www.ncbi.nlm.nih.gov/pubmed/33014170
http://dx.doi.org/10.3762/bjoc.16.191
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author Tkachuk, Viktor M
Lukianov, Oleh O
Vovk, Mykhailo V
Gillaizeau, Isabelle
Sukach, Volodymyr A
author_facet Tkachuk, Viktor M
Lukianov, Oleh O
Vovk, Mykhailo V
Gillaizeau, Isabelle
Sukach, Volodymyr A
author_sort Tkachuk, Viktor M
collection PubMed
description The Chan–Evans–Lam reaction of 1-unsubstituted 4-fluoroalkylpyrimidin-2(1Н)-ones with arylboronic acids is reported as a facile synthetic route to hitherto unavailable N1-(het)aryl and N1-alkenyl derivatives of the corresponding pyrimidines. An efficient C–N bond-forming process is also observed by using boronic acid pinacol esters as coupling partners in the presence of Cu(II) acetate and boric acid. The 4-fluoroalkyl group on the pyrimidine ring significantly assists in the formation of the target N1-substituted products, in contrast to the 4-methyl and 4-unsubstituted substrates which do not undergo N1-arylation under similar reaction conditions.
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spelling pubmed-75093802020-10-01 Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones Tkachuk, Viktor M Lukianov, Oleh O Vovk, Mykhailo V Gillaizeau, Isabelle Sukach, Volodymyr A Beilstein J Org Chem Full Research Paper The Chan–Evans–Lam reaction of 1-unsubstituted 4-fluoroalkylpyrimidin-2(1Н)-ones with arylboronic acids is reported as a facile synthetic route to hitherto unavailable N1-(het)aryl and N1-alkenyl derivatives of the corresponding pyrimidines. An efficient C–N bond-forming process is also observed by using boronic acid pinacol esters as coupling partners in the presence of Cu(II) acetate and boric acid. The 4-fluoroalkyl group on the pyrimidine ring significantly assists in the formation of the target N1-substituted products, in contrast to the 4-methyl and 4-unsubstituted substrates which do not undergo N1-arylation under similar reaction conditions. Beilstein-Institut 2020-09-17 /pmc/articles/PMC7509380/ /pubmed/33014170 http://dx.doi.org/10.3762/bjoc.16.191 Text en Copyright © 2020, Tkachuk et al. https://creativecommons.org/licenses/by/4.0https://www.beilstein-journals.org/bjoc/termsThis is an Open Access article under the terms of the Creative Commons Attribution License (https://creativecommons.org/licenses/by/4.0). Please note that the reuse, redistribution and reproduction in particular requires that the authors and source are credited. The license is subject to the Beilstein Journal of Organic Chemistry terms and conditions: (https://www.beilstein-journals.org/bjoc/terms)
spellingShingle Full Research Paper
Tkachuk, Viktor M
Lukianov, Oleh O
Vovk, Mykhailo V
Gillaizeau, Isabelle
Sukach, Volodymyr A
Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones
title Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones
title_full Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones
title_fullStr Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones
title_full_unstemmed Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones
title_short Chan–Evans–Lam N1-(het)arylation and N1-alkеnylation of 4-fluoroalkylpyrimidin-2(1H)-ones
title_sort chan–evans–lam n1-(het)arylation and n1-alkеnylation of 4-fluoroalkylpyrimidin-2(1h)-ones
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC7509380/
https://www.ncbi.nlm.nih.gov/pubmed/33014170
http://dx.doi.org/10.3762/bjoc.16.191
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