Palladium-catalyzed cross coupling reactions of 4-bromo-6H-1,2-oxazines

A number of 4-aryl- and 4-alkynyl-substituted 6H-1,2-oxazines 8 and 9 have been prepared in good yields via cross coupling reactions of halogenated precursors 2, which in turn are easily accessible by bromination of 6H-1,2-oxazines 1. Lewis-acid promoted reaction of 1,2-oxazine 9c with 1-hexyne prov...

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Detalles Bibliográficos
Autores principales: Zimmer, Reinhold, Schmidt, Elmar, Andrä, Michal, Duhs, Marcel-Antoine, Linder, Igor, Reissig, Hans-Ulrich
Formato: Texto
Lenguaje:English
Publicado: Beilstein-Institut 2009
Materias:
Preliminary Communication
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2779659/
https://www.ncbi.nlm.nih.gov/pubmed/19936264
http://dx.doi.org/10.3762/bjoc.5.44
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author Zimmer, Reinhold
Schmidt, Elmar
Andrä, Michal
Duhs, Marcel-Antoine
Linder, Igor
Reissig, Hans-Ulrich
author_facet Zimmer, Reinhold
Schmidt, Elmar
Andrä, Michal
Duhs, Marcel-Antoine
Linder, Igor
Reissig, Hans-Ulrich
author_sort Zimmer, Reinhold
collection PubMed
description A number of 4-aryl- and 4-alkynyl-substituted 6H-1,2-oxazines 8 and 9 have been prepared in good yields via cross coupling reactions of halogenated precursors 2, which in turn are easily accessible by bromination of 6H-1,2-oxazines 1. Lewis-acid promoted reaction of 1,2-oxazine 9c with 1-hexyne provided alkynyl-substituted pyridine derivative 12 thus demonstrating the potential of this approach for the synthesis of pyridines.
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spelling pubmed-27796592009-11-20 Palladium-catalyzed cross coupling reactions of 4-bromo-6H-1,2-oxazines Zimmer, Reinhold Schmidt, Elmar Andrä, Michal Duhs, Marcel-Antoine Linder, Igor Reissig, Hans-Ulrich Beilstein J Org Chem Preliminary Communication A number of 4-aryl- and 4-alkynyl-substituted 6H-1,2-oxazines 8 and 9 have been prepared in good yields via cross coupling reactions of halogenated precursors 2, which in turn are easily accessible by bromination of 6H-1,2-oxazines 1. Lewis-acid promoted reaction of 1,2-oxazine 9c with 1-hexyne provided alkynyl-substituted pyridine derivative 12 thus demonstrating the potential of this approach for the synthesis of pyridines. Beilstein-Institut 2009-09-16 /pmc/articles/PMC2779659/ /pubmed/19936264 http://dx.doi.org/10.3762/bjoc.5.44 Text en Copyright © 2009, Zimmer 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 Preliminary Communication
Zimmer, Reinhold
Schmidt, Elmar
Andrä, Michal
Duhs, Marcel-Antoine
Linder, Igor
Reissig, Hans-Ulrich
Palladium-catalyzed cross coupling reactions of 4-bromo-6H-1,2-oxazines
title Palladium-catalyzed cross coupling reactions of 4-bromo-6H-1,2-oxazines
title_full Palladium-catalyzed cross coupling reactions of 4-bromo-6H-1,2-oxazines
title_fullStr Palladium-catalyzed cross coupling reactions of 4-bromo-6H-1,2-oxazines
title_full_unstemmed Palladium-catalyzed cross coupling reactions of 4-bromo-6H-1,2-oxazines
title_short Palladium-catalyzed cross coupling reactions of 4-bromo-6H-1,2-oxazines
title_sort palladium-catalyzed cross coupling reactions of 4-bromo-6h-1,2-oxazines
topic Preliminary Communication
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC2779659/
https://www.ncbi.nlm.nih.gov/pubmed/19936264
http://dx.doi.org/10.3762/bjoc.5.44
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