Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines

A Chan–Lam reaction has been used to prepare N-alkenyl-α,β-unsaturated nitrones, which undergo a subsequent thermal rearrangement to the corresponding tri- and tetrasubstituted pyridines. The optimization and scope of these transformations is discussed. Initial mechanistic experiments suggest a reac...

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Detalles Bibliográficos
Autores principales: Kontokosta, Dimitra, Mueller, Daniel S, Mo, Dong-Liang, Pace, Wiktoria H, Simpson, Rachel A, Anderson, Laura L
Formato: Online Artículo Texto
Lenguaje:English
Publicado: Beilstein-Institut 2015
Materias:
Full Research Paper
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4660996/
https://www.ncbi.nlm.nih.gov/pubmed/26664630
http://dx.doi.org/10.3762/bjoc.11.226
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author Kontokosta, Dimitra
Mueller, Daniel S
Mo, Dong-Liang
Pace, Wiktoria H
Simpson, Rachel A
Anderson, Laura L
author_facet Kontokosta, Dimitra
Mueller, Daniel S
Mo, Dong-Liang
Pace, Wiktoria H
Simpson, Rachel A
Anderson, Laura L
author_sort Kontokosta, Dimitra
collection PubMed
description A Chan–Lam reaction has been used to prepare N-alkenyl-α,β-unsaturated nitrones, which undergo a subsequent thermal rearrangement to the corresponding tri- and tetrasubstituted pyridines. The optimization and scope of these transformations is discussed. Initial mechanistic experiments suggest a reaction pathway involving oxygen transfer followed by cyclization.
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spelling pubmed-46609962015-12-09 Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines Kontokosta, Dimitra Mueller, Daniel S Mo, Dong-Liang Pace, Wiktoria H Simpson, Rachel A Anderson, Laura L Beilstein J Org Chem Full Research Paper A Chan–Lam reaction has been used to prepare N-alkenyl-α,β-unsaturated nitrones, which undergo a subsequent thermal rearrangement to the corresponding tri- and tetrasubstituted pyridines. The optimization and scope of these transformations is discussed. Initial mechanistic experiments suggest a reaction pathway involving oxygen transfer followed by cyclization. Beilstein-Institut 2015-11-04 /pmc/articles/PMC4660996/ /pubmed/26664630 http://dx.doi.org/10.3762/bjoc.11.226 Text en Copyright © 2015, Kontokosta 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
Kontokosta, Dimitra
Mueller, Daniel S
Mo, Dong-Liang
Pace, Wiktoria H
Simpson, Rachel A
Anderson, Laura L
Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
title Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
title_full Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
title_fullStr Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
title_full_unstemmed Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
title_short Copper-mediated synthesis of N-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
title_sort copper-mediated synthesis of n-alkenyl-α,β-unsaturated nitrones and their conversion to tri- and tetrasubstituted pyridines
topic Full Research Paper
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC4660996/
https://www.ncbi.nlm.nih.gov/pubmed/26664630
http://dx.doi.org/10.3762/bjoc.11.226
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