Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates

ABSTRACT: A regioselective synthesis of pyridines by the addition of malonate anions to pyridine N-oxide derivatives, which have been activated by trifluoromethanesulfonic anhydride, is reported. The reaction selectively affords either 2- or 4-substituted pyridines in good yields. GRAPHICAL ABSTRACT...

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Detalles Bibliográficos
Autores principales: Lemmerer, Miran, Teskey, Christopher J., Kaiser, Daniel, Maulide, Nuno
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Springer Vienna 2017
Materias:
Short Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5906502/
https://www.ncbi.nlm.nih.gov/pubmed/29681655
http://dx.doi.org/10.1007/s00706-017-2081-y
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author Lemmerer, Miran
Teskey, Christopher J.
Kaiser, Daniel
Maulide, Nuno
author_facet Lemmerer, Miran
Teskey, Christopher J.
Kaiser, Daniel
Maulide, Nuno
author_sort Lemmerer, Miran
collection PubMed
description ABSTRACT: A regioselective synthesis of pyridines by the addition of malonate anions to pyridine N-oxide derivatives, which have been activated by trifluoromethanesulfonic anhydride, is reported. The reaction selectively affords either 2- or 4-substituted pyridines in good yields. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-017-2081-y) contains supplementary material, which is available to authorized users.
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spelling pubmed-59065022018-04-20 Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates Lemmerer, Miran Teskey, Christopher J. Kaiser, Daniel Maulide, Nuno Monatsh Chem Short Communication ABSTRACT: A regioselective synthesis of pyridines by the addition of malonate anions to pyridine N-oxide derivatives, which have been activated by trifluoromethanesulfonic anhydride, is reported. The reaction selectively affords either 2- or 4-substituted pyridines in good yields. GRAPHICAL ABSTRACT: [Image: see text] ELECTRONIC SUPPLEMENTARY MATERIAL: The online version of this article (10.1007/s00706-017-2081-y) contains supplementary material, which is available to authorized users. Springer Vienna 2017-11-28 2018 /pmc/articles/PMC5906502/ /pubmed/29681655 http://dx.doi.org/10.1007/s00706-017-2081-y Text en © The Author(s) 2018 Open AccessThis article is distributed under the terms of the Creative Commons Attribution 4.0 International License (http://creativecommons.org/licenses/by/4.0/), which permits unrestricted use, distribution, and reproduction in any medium, provided you give appropriate credit to the original author(s) and the source, provide a link to the Creative Commons license, and indicate if changes were made.
spellingShingle Short Communication
Lemmerer, Miran
Teskey, Christopher J.
Kaiser, Daniel
Maulide, Nuno
Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates
title Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates
title_full Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates
title_fullStr Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates
title_full_unstemmed Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates
title_short Regioselective synthesis of pyridines by redox alkylation of pyridine N-oxides with malonates
title_sort regioselective synthesis of pyridines by redox alkylation of pyridine n-oxides with malonates
topic Short Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC5906502/
https://www.ncbi.nlm.nih.gov/pubmed/29681655
http://dx.doi.org/10.1007/s00706-017-2081-y
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AT kaiserdaniel regioselectivesynthesisofpyridinesbyredoxalkylationofpyridinenoxideswithmalonates
AT maulidenuno regioselectivesynthesisofpyridinesbyredoxalkylationofpyridinenoxideswithmalonates

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