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Selective C‐7 Functionalization of Phenanthridines by Microwave‐Assisted Claisen Rearrangements of 8‐Allyloxyphenanthridines

Carbon‐carbon bond formation in the phenanthridine 7‐position was achieved by microwave‐assisted Claisen rearrangement of 8‐allyloxyphenanthridines. The reactions took place with excellent regioselectivity and high chemical yields. If the 7‐position was substituted, rearrangement to C‐9 took place,...

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Autores principales: Lepsøe, Mathias Ryslett, Dalevold, Aleksander Granum, Gundersen, Lise‐Lotte
Formato: Online Artículo Texto
Lenguaje:English
Publicado: John Wiley and Sons Inc. 2023
Materias:
Acceso en línea:https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10362114/
https://www.ncbi.nlm.nih.gov/pubmed/37480187
http://dx.doi.org/10.1002/open.202300095
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author Lepsøe, Mathias Ryslett
Dalevold, Aleksander Granum
Gundersen, Lise‐Lotte
author_facet Lepsøe, Mathias Ryslett
Dalevold, Aleksander Granum
Gundersen, Lise‐Lotte
author_sort Lepsøe, Mathias Ryslett
collection PubMed
description Carbon‐carbon bond formation in the phenanthridine 7‐position was achieved by microwave‐assisted Claisen rearrangement of 8‐allyloxyphenanthridines. The reactions took place with excellent regioselectivity and high chemical yields. If the 7‐position was substituted, rearrangement to C‐9 took place, but the reaction occurred less readily. Rearrangements of 8‐allyloxy‐5,6‐dihydrophenanthridines (phenanthridines with a saturated B‐ring) gave a mixture of 7‐ and 9‐substituted products. The experimental results were supported by DFT (density functional theory) calculations.
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spelling pubmed-103621142023-07-23 Selective C‐7 Functionalization of Phenanthridines by Microwave‐Assisted Claisen Rearrangements of 8‐Allyloxyphenanthridines Lepsøe, Mathias Ryslett Dalevold, Aleksander Granum Gundersen, Lise‐Lotte ChemistryOpen Research Articles Carbon‐carbon bond formation in the phenanthridine 7‐position was achieved by microwave‐assisted Claisen rearrangement of 8‐allyloxyphenanthridines. The reactions took place with excellent regioselectivity and high chemical yields. If the 7‐position was substituted, rearrangement to C‐9 took place, but the reaction occurred less readily. Rearrangements of 8‐allyloxy‐5,6‐dihydrophenanthridines (phenanthridines with a saturated B‐ring) gave a mixture of 7‐ and 9‐substituted products. The experimental results were supported by DFT (density functional theory) calculations. John Wiley and Sons Inc. 2023-07-21 /pmc/articles/PMC10362114/ /pubmed/37480187 http://dx.doi.org/10.1002/open.202300095 Text en © 2023 The Authors. ChemistryOpen published by Wiley-VCH GmbH https://creativecommons.org/licenses/by/4.0/This is an open access article under the terms of the http://creativecommons.org/licenses/by/4.0/ (https://creativecommons.org/licenses/by/4.0/) License, which permits use, distribution and reproduction in any medium, provided the original work is properly cited.
spellingShingle Research Articles
Lepsøe, Mathias Ryslett
Dalevold, Aleksander Granum
Gundersen, Lise‐Lotte
Selective C‐7 Functionalization of Phenanthridines by Microwave‐Assisted Claisen Rearrangements of 8‐Allyloxyphenanthridines
title Selective C‐7 Functionalization of Phenanthridines by Microwave‐Assisted Claisen Rearrangements of 8‐Allyloxyphenanthridines
title_full Selective C‐7 Functionalization of Phenanthridines by Microwave‐Assisted Claisen Rearrangements of 8‐Allyloxyphenanthridines
title_fullStr Selective C‐7 Functionalization of Phenanthridines by Microwave‐Assisted Claisen Rearrangements of 8‐Allyloxyphenanthridines
title_full_unstemmed Selective C‐7 Functionalization of Phenanthridines by Microwave‐Assisted Claisen Rearrangements of 8‐Allyloxyphenanthridines
title_short Selective C‐7 Functionalization of Phenanthridines by Microwave‐Assisted Claisen Rearrangements of 8‐Allyloxyphenanthridines
title_sort selective c‐7 functionalization of phenanthridines by microwave‐assisted claisen rearrangements of 8‐allyloxyphenanthridines
topic Research Articles
url https://www.ncbi.nlm.nih.gov/pmc/articles/PMC10362114/
https://www.ncbi.nlm.nih.gov/pubmed/37480187
http://dx.doi.org/10.1002/open.202300095
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