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

Claisen rearrangement DFT calculations microwave chemistry nitrogen heterocycles phenanthridines

Journal

ChemistryOpen

ISSN: 2191-1363

Titre abrégé: ChemistryOpen

Pays: Germany

ID NLM: 101594811

Informations de publication

Date de publication:
Jul 2023

Historique:

revised: 16 06 2023

received: 02 06 2023

medline: 22 7 2023

pubmed: 22 7 2023

entrez: 22 7 2023

Statut: ppublish

Résumé

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.

Identifiants

DOI: 10.1002/open.202300095 PMID: 37480187 PMC: PMC10362114

pubmed: 37480187

doi: 10.1002/open.202300095

pmc: PMC10362114

doi:

Types de publication

Journal Article

Langues

eng

Sous-ensembles de citation

Pagination

e202300095

Subventions

Organisme : Department of Chemistry, University of Oslo

Organisme : Research Council of Norway

Organisme : Norwegian NMR Package

Organisme : Department of Chemistry and the Faculty of Mathematics and Natural Sciences at University of Oslo

Informations de copyright

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