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A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction

A practical approach to highly functionalized 4-hydroxypyridine derivatives with stereogenic side chains in the 2- and 6-positions is described. The presented two-step process utilizes a multicomponent reaction of alkoxyallenes, nitriles and carboxylic acids to provide β-methoxy-β-ketoenamides which...

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Autores principales: Eidamshaus, Christian, Kumar, Roopender, Bera, Mrinal K, Reissig, Hans-Ulrich
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2011
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3170199/
https://www.ncbi.nlm.nih.gov/pubmed/21915195
http://dx.doi.org/10.3762/bjoc.7.108
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author Eidamshaus, Christian
Kumar, Roopender
Bera, Mrinal K
Reissig, Hans-Ulrich
author_facet Eidamshaus, Christian
Kumar, Roopender
Bera, Mrinal K
Reissig, Hans-Ulrich
author_sort Eidamshaus, Christian
collection PubMed
description A practical approach to highly functionalized 4-hydroxypyridine derivatives with stereogenic side chains in the 2- and 6-positions is described. The presented two-step process utilizes a multicomponent reaction of alkoxyallenes, nitriles and carboxylic acids to provide β-methoxy-β-ketoenamides which are transformed into 4-hydroxypyridines in a subsequent cyclocondensation. The process shows broad substrate scope and leads to differentially substituted enantiopure pyridines in good to moderate yields. The preparation of diverse substituted lactic acid derived pyrid-4-yl nonaflates is described. Additional evidence for the postulated mechanism of the multicomponent reaction is presented.
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spelling pubmed-31701992011-09-13 A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction Eidamshaus, Christian Kumar, Roopender Bera, Mrinal K Reissig, Hans-Ulrich Beilstein J Org Chem Full Research Paper A practical approach to highly functionalized 4-hydroxypyridine derivatives with stereogenic side chains in the 2- and 6-positions is described. The presented two-step process utilizes a multicomponent reaction of alkoxyallenes, nitriles and carboxylic acids to provide β-methoxy-β-ketoenamides which are transformed into 4-hydroxypyridines in a subsequent cyclocondensation. The process shows broad substrate scope and leads to differentially substituted enantiopure pyridines in good to moderate yields. The preparation of diverse substituted lactic acid derived pyrid-4-yl nonaflates is described. Additional evidence for the postulated mechanism of the multicomponent reaction is presented. Beilstein-Institut 2011-07-13 /pmc/articles/PMC3170199/ /pubmed/21915195 http://dx.doi.org/10.3762/bjoc.7.108 Text en Copyright © 2011, Eidamshaus et al. https://creativecommons.org/licenses/by/2.0https://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/2.0), which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited. 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
Eidamshaus, Christian
Kumar, Roopender
Bera, Mrinal K
Reissig, Hans-Ulrich
A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction
title A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction
title_full A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction
title_fullStr A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction
title_full_unstemmed A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction
title_short A practical two-step procedure for the preparation of enantiopure pyridines: Multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction
title_sort practical two-step procedure for the preparation of enantiopure pyridines: multicomponent reactions of alkoxyallenes, nitriles and carboxylic acids followed by a cyclocondensation reaction
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC3170199/
https://www.ncbi.nlm.nih.gov/pubmed/21915195
http://dx.doi.org/10.3762/bjoc.7.108
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