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Tandem Ring Opening/Intramolecular [2 + 2] Cycloaddition Reaction for the Synthesis of Cyclobutane Fused Thiazolino-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.ORCID iD: 0000-0002-4480-1219
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2021 (English)In: Journal of Organic Chemistry, ISSN 0022-3263, E-ISSN 1520-6904, Vol. 86, no 23, p. 16582-16592Article in journal (Refereed) Published
Abstract [en]

Reaction of thiazoline fused 2-pyridones with alkyl halides in the presence of cesium carbonate opens the thiazoline ring via S-alkylation and generates N-alkenyl functionalized 2-pyridones. In the reaction with propargyl bromide, the thiazoline ring opens and subsequently closes via a [2 + 2] cycloaddition between an in situ generated allene and the α,β-unsaturated methyl ester. This method enabled the synthesis of a variety of cyclobutane fused thiazolino-2-pyridones, of which a few analogues inhibit amyloid β1–40 fibril formation. Furthermore, other analogues were able to bind mature α-synuclein and amyloid β1−40 fibrils. Several thiazoline fused 2-pyridones with biological activity tolerate this transformation, which in addition provides an exocyclic alkene as a potential handle for tuning bioactivity.

Place, publisher, year, edition, pages
American Chemical Society (ACS), 2021. Vol. 86, no 23, p. 16582-16592
National Category
Organic Chemistry
Identifiers
URN: urn:nbn:se:umu:diva-189656DOI: 10.1021/acs.joc.1c01875ISI: 000752848600030PubMedID: 34767366Scopus ID: 2-s2.0-85119436020OAI: oai:DiVA.org:umu-189656DiVA, id: diva2:1612375
Funder
Swedish Research Council, 2017-02339Swedish Research Council, 2017-00695Swedish Research Council, 2018-04589Knut and Alice Wallenberg Foundation, 2013.0031Göran Gustafsson Foundation for Research in Natural Sciences and MedicineThe Kempe Foundations, SMK-1755Swedish Foundation for Strategic Research , SB12-0070NIH (National Institute of Health), (R01AI134847-01A1Familjen Erling-Perssons StiftelseAvailable from: 2021-11-18 Created: 2021-11-18 Last updated: 2023-09-05Bibliographically approved

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Tyagi, MohitAdolfsson, Dan E.Singh, PardeepÅdén, JörgenJayaweera, Sanduni WasanaGharibyan, AnnaBharate, Jaideep B.Kiss, AnitaSarkar, SouvikOlofsson, AndersAlmqvist, Fredrik

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Tyagi, MohitAdolfsson, Dan E.Singh, PardeepÅdén, JörgenJayaweera, Sanduni WasanaGharibyan, AnnaBharate, Jaideep B.Kiss, AnitaSarkar, SouvikOlofsson, AndersAlmqvist, Fredrik
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Department of ChemistryDepartment of Medical Biochemistry and Biophysics
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Journal of Organic Chemistry
Organic Chemistry

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