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An Enantioselective Ketene-Imine Cycloaddition Method for Synthesis of Substituted Ring-Fused 2-Pyridinones
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.
2001 (English)In: The Journal of Organic Chemistry, Vol. 66, no 20, p. 6756-61Article in journal (Refereed) Published
Abstract [en]

Previously, a method for the stereoselective synthesis of -lactams, starting from 2H-2-thiazolines and Meldrum's acid derivatives, has been reported from our laboratory. We now report a new method for the synthesis of optically active, highly substituted ring-fused 2-pyridinones. This was discovered when 2-alkyl-2-thiazolines and Meldrum's acid derivatives were treated with HCl(g) in benzene at 5 78 C. Further refinement of the synthetic protocol revealed that use of 1,2-dichloroethane as solvent at 0 64 C led to the desired 2-pyridinones in good yields and with excellent enantioselectivity. Use of these conditions allowed preparation of 2-pyridinones from several different 2-thiazolines and Meldrum's acid derivatives and may be a general route to 2-pyridinones.

Place, publisher, year, edition, pages
2001. Vol. 66, no 20, p. 6756-61
National Category
Chemical Sciences
Identifiers
URN: urn:nbn:se:umu:diva-9584DOI: doi:10.1021/jo015794uOAI: oai:DiVA.org:umu-9584DiVA, id: diva2:149255
Available from: 2008-04-28 Created: 2008-04-28 Last updated: 2018-06-09Bibliographically approved
In thesis
1. Synthesis and biological evaluation of Bicyclic β-Lactams and 2-Pyridinones: Pilicides Targeting Pilus Biogenesis in Pathogenic Bacteria
Open this publication in new window or tab >>Synthesis and biological evaluation of Bicyclic β-Lactams and 2-Pyridinones: Pilicides Targeting Pilus Biogenesis in Pathogenic Bacteria
2003 (English)Doctoral thesis, comprehensive summary (Other academic)
Abstract [en]

New methods have been developed for the synthesis of bicyclic β-lactams and 2-pyridinones by combining acyl Meldrum’s acids and Δ2-thiazolines. The 2-pyridinones were synthesised both in solution using conventional heating or microwave assisted heating as well as by solid supported chemistry.

The compounds (pilicides) were designed to interfere with the assembly of pili in uropathogenic E. coli by inhibiting the periplasmic chaperones. The affinity of the pilicides to the chaperones was investigated with surface plasmon resonance technique (Biacore) and with relaxation-edited 1H NMR spectroscopy experiments. Finally, the pilicides were investigated for their ability to inhibit pili formation in uropathogenic E. coli in a hemagglutination assay, where members of the 2-pyridinone family proved to be able to cause depiliation.

Place, publisher, year, edition, pages
Umeå: Department of Chemistry, Organic Chemistry, Umeå University, 2003. p. 75
Keyword
Organic chemistry, β-lactam, 2-pyridinone, 2-pyridone, Meldrum’s acid, Δ2-thiazoline, solid-phase synthesis, microwave assisted synthesis, antibacterial, pili, pilicide, Organisk kemi
National Category
Organic Chemistry
Research subject
Organic Chemistry
Identifiers
urn:nbn:se:umu:diva-165 (URN)91-7305-546-8 (ISBN)
Public defence
2003-12-19, Stora Hörsalen, KBC-huset,, Umeå universitet, Umeå, 13:00 (English)
Opponent
Available from: 2003-11-28 Created: 2003-11-28 Last updated: 2018-03-15Bibliographically approved

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Almqvist, Fredrik

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