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Photoredox-catalyzed radical coupling of C7-chloromethyl-substituted thiazolino ring-fused 2-pyridones with quinoxalinones
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Department of Applied Physics, Royal Institute of Technology (KTH), Stockholm, Sweden.
Department of Applied Physics, Royal Institute of Technology (KTH), Stockholm, Sweden.
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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
Identifiers
URN: urn:nbn:se:umu:diva-228520DOI: 10.1021/acs.joc.4c01224ISI: 001277913700001PubMedID: 39051977Scopus ID: 2-s2.0-85199692853OAI: oai:DiVA.org:umu-228520DiVA, id: diva2:1889683
Funder
NIH (National Institutes of Health), R01AI134847-01A1NIH (National Institutes of Health), 1U19AI157797-01Familjen Erling-Perssons Stiftelse, P20-00473Swedish Research Council, 2018-04589Swedish Research Council, 2021-05040JSwedish Research Council, VR C114766193The Kempe Foundations, SMK-1755Available from: 2024-08-16 Created: 2024-08-16 Last updated: 2024-08-16Bibliographically approved

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Hellgren, VictorSingh, PardeepManavalan, GopinathanAlmqvist, Fredrik

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