Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions

A series of trifluoromethyl-substituted 3-alkoxypyridinol derivatives has been deprotected to furnish pyridine-3,4-diol derivatives in good yields. The X-ray crystal structure analysis proved that a 1:1 mixture of pyridine-3,4-diols and their pyridin-4-one tautomers exist in the solid state. Subsequ...

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Autores principales: Lechel, Tilman, Brüdgam, Irene, Reissig, Hans-Ulrich
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2010
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874341/
https://www.ncbi.nlm.nih.gov/pubmed/20502600
http://dx.doi.org/10.3762/bjoc.6.42
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author Lechel, Tilman
Brüdgam, Irene
Reissig, Hans-Ulrich
author_facet Lechel, Tilman
Brüdgam, Irene
Reissig, Hans-Ulrich
author_sort Lechel, Tilman
collection PubMed
description A series of trifluoromethyl-substituted 3-alkoxypyridinol derivatives has been deprotected to furnish pyridine-3,4-diol derivatives in good yields. The X-ray crystal structure analysis proved that a 1:1 mixture of pyridine-3,4-diols and their pyridin-4-one tautomers exist in the solid state. Subsequent conversion into bis(perfluoroalkanesulfonate)s were smoothly achieved. The obtained compounds were used as substrates for palladium-catalyzed coupling reactions. Fluorescence measurements of the biscoupled products showed a maximum of emission in the violet region of the spectrum.
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spelling pubmed-28743412010-05-25 Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions Lechel, Tilman Brüdgam, Irene Reissig, Hans-Ulrich Beilstein J Org Chem Full Research Paper A series of trifluoromethyl-substituted 3-alkoxypyridinol derivatives has been deprotected to furnish pyridine-3,4-diol derivatives in good yields. The X-ray crystal structure analysis proved that a 1:1 mixture of pyridine-3,4-diols and their pyridin-4-one tautomers exist in the solid state. Subsequent conversion into bis(perfluoroalkanesulfonate)s were smoothly achieved. The obtained compounds were used as substrates for palladium-catalyzed coupling reactions. Fluorescence measurements of the biscoupled products showed a maximum of emission in the violet region of the spectrum. Beilstein-Institut 2010-04-29 /pmc/articles/PMC2874341/ /pubmed/20502600 http://dx.doi.org/10.3762/bjoc.6.42 Text en Copyright © 2010, Lechel 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
Lechel, Tilman
Brüdgam, Irene
Reissig, Hans-Ulrich
Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions
title Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions
title_full Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions
title_fullStr Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions
title_full_unstemmed Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions
title_short Preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions
title_sort preparation of pyridine-3,4-diols, their crystal packing and their use as precursors for palladium-catalyzed cross-coupling reactions
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2874341/
https://www.ncbi.nlm.nih.gov/pubmed/20502600
http://dx.doi.org/10.3762/bjoc.6.42
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AT brudgamirene preparationofpyridine34diolstheircrystalpackingandtheiruseasprecursorsforpalladiumcatalyzedcrosscouplingreactions
AT reissighansulrich preparationofpyridine34diolstheircrystalpackingandtheiruseasprecursorsforpalladiumcatalyzedcrosscouplingreactions

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