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Synthesis of Densely Functionalized N-Alkenyl 2-Pyridones via Benzyne-Induced Ring Opening of Thiazolino-Fused 2-Pyridones
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
Umeå University, Faculty of Science and Technology, Department of Chemistry.
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2019 (English)In: Organic Letters, ISSN 1523-7060, E-ISSN 1523-7052Article in journal (Refereed) Epub ahead of print
Abstract [en]

We report the synthesis of 6-arylthio-substituted-N-alkenyl 2-pyridones by ring opening of bicyclic thiazolino-2-pyridones with arynes. Varied functionalization was used to investigate scope and substituent influences on reactivity. Selected conditions favor thioether ring opening over [4 + 2] cycloaddition and an unusual aryne incorporating ring expansion. Deuterium labeling was used to clarify observed reactivity. Using the knowledge, we produced drug-like molecules with complex substitution patterns and show how thioether ring opening can be used on scaffolds with competing reactivities.

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American Chemical Society (ACS), 2019.
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Organic Chemistry Inorganic Chemistry Polymer Chemistry
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URN: urn:nbn:se:umu:diva-162826DOI: 10.1021/acs.orglett.9b02549PubMedID: 31419146OAI: oai:DiVA.org:umu-162826DiVA, id: diva2:1347074
Available from: 2019-08-30 Created: 2019-08-30 Last updated: 2019-09-03

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Singh, PardeepCairns, Andrew G.Adolfsson, Dan E.Ådén, JörgenSauer, Uwe H.Almqvist, Fredrik

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Singh, PardeepCairns, Andrew G.Adolfsson, Dan E.Ådén, JörgenSauer, Uwe H.Almqvist, Fredrik
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