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Photoredox-Catalyzed Radical Coupling of C7-Chloromethyl-Substituted Thiazolino Ring-Fused 2-Pyridones with Quinoxalinones
Department of Chemistry, Umeå University, SE-90187 Umeå, Sweden.
Department of Chemistry, Umeå University, SE-90187 Umeå, Sweden.
KTH, School of Engineering Sciences (SCI), Applied Physics, Bio-Opto-Nano Physics.
KTH, School of Engineering Sciences (SCI), Applied Physics, Bio-Opto-Nano Physics.ORCID iD: 0000-0002-2922-1566
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2024 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 89, no 16, p. 11802-11810Article in journal (Refereed) Published
Abstract [en]

We have developed an Ir(PPy)3 photoredox-catalyzed cross-coupling reaction that allows installation of quinoxalinones at the C7 position of thiazolino ring-fused 2-pyridones (TRPs) under mild conditions. The methodology tolerates various substituted quinoxalinones and biologically relevant substituents on the C8 position of the TRP. The TRP scaffold has large potential in the development of lead compounds, and while the coupled products are interesting from a drug-development perspective, the methodology will be useful for developing more potent and drug-like TRP-based candidates.

Place, publisher, year, edition, pages
American Chemical Society (ACS) , 2024. Vol. 89, no 16, p. 11802-11810
National Category
Organic Chemistry
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URN: urn:nbn:se:kth:diva-366652DOI: 10.1021/acs.joc.4c01224ISI: 001277913700001PubMedID: 39051977Scopus ID: 2-s2.0-85199692853OAI: oai:DiVA.org:kth-366652DiVA, id: diva2:1982788
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QC 20250708

Available from: 2025-07-08 Created: 2025-07-08 Last updated: 2025-07-08Bibliographically approved

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Kulkarni, AbhilashBagheri, NiushaWidengren, Jerker

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