Exploring Synthetic Strategies for 1H-Indazoles and Their N-Oxides: Electrochemical Synthesis of 1H-Indazole N-Oxides and Their Divergent C-H Functionalizations.
C−H Functionalization
Divergent
Electrochemical
Paired Electrolysis
Radicals
Journal
Angewandte Chemie (International ed. in English)
ISSN: 1521-3773
Titre abrégé: Angew Chem Int Ed Engl
Pays: Germany
ID NLM: 0370543
Informations de publication
Date de publication:
26 Jun 2023
26 Jun 2023
Historique:
received:
08
03
2023
medline:
22
4
2023
pubmed:
22
4
2023
entrez:
22
04
2023
Statut:
ppublish
Résumé
The selective electrochemical synthesis of 1H-indazoles and their N-oxides and the subsequent C-H functionalization of the 1H-indazole N-oxides are described. The electrochemical outcomes were determined by the nature of the cathode material. When a reticulated vitreous carbon cathode was used, a wide range of 1H-indazole N-oxides were selectively synthesized, and the electrosynthesis products were deoxygenated to N-heteroaromatics, owing to cathodic cleavage of the N-O bond via paired electrolysis, when a Zn cathode was used. The scope of this electrochemical protocol is broad, as both electron-rich and electron-poor substrates were tolerated. The potency of this electrochemical strategy was demonstrated through the late-stage functionalization of various bioactive molecules, making this reaction attractive for the synthesis of 1H-indazole derivatives for pharmaceutical research and development. Detailed mechanistic investigations involving electron paramagnetic resonance spectroscopy and cyclic voltammetry suggested a radical pathway featuring iminoxyl radicals. Owing to the rich reactivity of 1H-indazole N-oxides, diverse C-H functionalization reactions were performed. We demonstrated the synthetic utility of 1H-indazole N-oxides by synthesizing the pharmaceutical molecules lificiguat and YD (3); key intermediates for bendazac, benzydamine, norepinephrine/serotonin reuptake inhibitors, SAM-531, and gamendazole analogues; and a precursor for organic light-emitting diodes.
Identifiants
pubmed: 37086084
doi: 10.1002/anie.202303460
doi:
Substances chimiques
Oxides
0
Indazoles
0
Pharmaceutical Preparations
0
Types de publication
Journal Article
Langues
eng
Sous-ensembles de citation
IM
Pagination
e202303460Subventions
Organisme : National Research Foundation of Korea
ID : 2019R1A2C2004902
Organisme : National Research Foundation of Korea
ID : 2022R1A4A2000778
Organisme : Samsung Science and Technology Foundation
ID : SSTF-BA190113746
Informations de copyright
© 2023 Wiley-VCH GmbH.
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